<?xml version="1.0" encoding="UTF-8"?>

<!--XBRL Document Created with Wdesk from Workiva-->
<!--Copyright 2022 Workiva-->
<!--r:70612274-0d95-43da-88b6-045ecfc396b7,g:e54e3cb1-353f-43de-856a-3d85b5ecf5db-->
<link:linkbase xmlns:link="http://www.xbrl.org/2003/linkbase" xmlns:xlink="http://www.w3.org/1999/xlink" xmlns:xsi="http://www.w3.org/2001/XMLSchema-instance" xsi:schemaLocation="http://www.xbrl.org/2003/linkbase http://www.xbrl.org/2003/xbrl-linkbase-2003-12-31.xsd">
  <link:roleRef roleURI="http://www.xbrl.org/2009/role/negatedPeriodStartLabel" xlink:type="simple" xlink:href="http://www.xbrl.org/lrr/role/negated-2009-12-16.xsd#negatedPeriodStartLabel"/>
  <link:roleRef roleURI="http://www.xbrl.org/2009/role/netLabel" xlink:type="simple" xlink:href="http://www.xbrl.org/lrr/role/net-2009-12-16.xsd#netLabel"/>
  <link:roleRef roleURI="http://www.xbrl.org/2009/role/negatedNetLabel" xlink:type="simple" xlink:href="http://www.xbrl.org/lrr/role/negated-2009-12-16.xsd#negatedNetLabel"/>
  <link:roleRef roleURI="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="simple" xlink:href="http://www.xbrl.org/lrr/role/negated-2009-12-16.xsd#negatedTerseLabel"/>
  <link:roleRef roleURI="http://www.xbrl.org/2009/role/negatedPeriodEndLabel" xlink:type="simple" xlink:href="http://www.xbrl.org/lrr/role/negated-2009-12-16.xsd#negatedPeriodEndLabel"/>
  <link:roleRef roleURI="http://www.xbrl.org/2009/role/negatedLabel" xlink:type="simple" xlink:href="http://www.xbrl.org/lrr/role/negated-2009-12-16.xsd#negatedLabel"/>
  <link:roleRef roleURI="http://www.xbrl.org/2009/role/negatedTotalLabel" xlink:type="simple" xlink:href="http://www.xbrl.org/lrr/role/negated-2009-12-16.xsd#negatedTotalLabel"/>
  <link:labelLink xlink:role="http://www.xbrl.org/2003/role/link" xlink:type="extended">
    <link:label id="lab_us-gaap_GeographicConcentrationRiskMember_ed20af7b-1f4b-48a3-940e-1a98d8277c85_terseLabel_en-US" xlink:label="lab_us-gaap_GeographicConcentrationRiskMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Geographic Concentration Risk</link:label>
    <link:label id="lab_us-gaap_GeographicConcentrationRiskMember_label_en-US" xlink:label="lab_us-gaap_GeographicConcentrationRiskMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Geographic Concentration Risk [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_GeographicConcentrationRiskMember" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_GeographicConcentrationRiskMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_GeographicConcentrationRiskMember" xlink:to="lab_us-gaap_GeographicConcentrationRiskMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesWithinOneYearFairValue_0633ddb8-658d-44b7-b589-fb863bd200c1_terseLabel_en-US" xlink:label="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesWithinOneYearFairValue" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Due in one year or less</link:label>
    <link:label id="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesWithinOneYearFairValue_label_en-US" xlink:label="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesWithinOneYearFairValue" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt Securities, Available-for-Sale, Fair Value, Maturity, Allocated and Single Maturity Date, Year One</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesWithinOneYearFairValue" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_AvailableForSaleSecuritiesDebtMaturitiesWithinOneYearFairValue"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesWithinOneYearFairValue" xlink:to="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesWithinOneYearFairValue" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_IncreaseDecreaseInReinsuranceRecoverable_362feab4-cca4-4d5d-b36d-0091c23088e7_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_IncreaseDecreaseInReinsuranceRecoverable" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Reinsurance recoverable and receivable</link:label>
    <link:label id="lab_us-gaap_IncreaseDecreaseInReinsuranceRecoverable_label_en-US" xlink:label="lab_us-gaap_IncreaseDecreaseInReinsuranceRecoverable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Increase (Decrease) in Reinsurance Recoverable</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncreaseDecreaseInReinsuranceRecoverable" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_IncreaseDecreaseInReinsuranceRecoverable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IncreaseDecreaseInReinsuranceRecoverable" xlink:to="lab_us-gaap_IncreaseDecreaseInReinsuranceRecoverable" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_IncreaseDecreaseInStockholdersEquityRollForward_a9efaff1-ff70-4beb-98d5-5affd475a88a_terseLabel_en-US" xlink:label="lab_us-gaap_IncreaseDecreaseInStockholdersEquityRollForward" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Increase (Decrease) in Stockholders' Equity [Roll Forward]</link:label>
    <link:label id="lab_us-gaap_IncreaseDecreaseInStockholdersEquityRollForward_label_en-US" xlink:label="lab_us-gaap_IncreaseDecreaseInStockholdersEquityRollForward" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Increase (Decrease) in Stockholders' Equity [Roll Forward]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncreaseDecreaseInStockholdersEquityRollForward" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_IncreaseDecreaseInStockholdersEquityRollForward"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IncreaseDecreaseInStockholdersEquityRollForward" xlink:to="lab_us-gaap_IncreaseDecreaseInStockholdersEquityRollForward" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ScheduleOfCashAndCashEquivalentsTableTextBlock_7ff989e5-952c-415b-9672-10574d467a99_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfCashAndCashEquivalentsTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Schedule of Cash and Cash Equivalents</link:label>
    <link:label id="lab_us-gaap_ScheduleOfCashAndCashEquivalentsTableTextBlock_label_en-US" xlink:label="lab_us-gaap_ScheduleOfCashAndCashEquivalentsTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Schedule of Cash and Cash Equivalents [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfCashAndCashEquivalentsTableTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ScheduleOfCashAndCashEquivalentsTableTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ScheduleOfCashAndCashEquivalentsTableTextBlock" xlink:to="lab_us-gaap_ScheduleOfCashAndCashEquivalentsTableTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DebtInstrumentCarryingAmount_6b315cb2-f7b5-45b5-831e-4a3fb08023aa_terseLabel_en-US" xlink:label="lab_us-gaap_DebtInstrumentCarryingAmount" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Term Loan</link:label>
    <link:label id="lab_us-gaap_DebtInstrumentCarryingAmount_label_en-US" xlink:label="lab_us-gaap_DebtInstrumentCarryingAmount" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Long-Term Debt, Gross</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtInstrumentCarryingAmount" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_DebtInstrumentCarryingAmount"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DebtInstrumentCarryingAmount" xlink:to="lab_us-gaap_DebtInstrumentCarryingAmount" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleUnrealizedLossPositionFairValueTableTextBlock_3a8bb54a-6fce-4e20-8498-ee1689ef55ef_terseLabel_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleUnrealizedLossPositionFairValueTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Schedule of Unrealized Losses</link:label>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleUnrealizedLossPositionFairValueTableTextBlock_label_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleUnrealizedLossPositionFairValueTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt Securities, Available-for-Sale, Unrealized Loss Position, Fair Value [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtSecuritiesAvailableForSaleUnrealizedLossPositionFairValueTableTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_DebtSecuritiesAvailableForSaleUnrealizedLossPositionFairValueTableTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DebtSecuritiesAvailableForSaleUnrealizedLossPositionFairValueTableTextBlock" xlink:to="lab_us-gaap_DebtSecuritiesAvailableForSaleUnrealizedLossPositionFairValueTableTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_EntityAddressPostalZipCode_d6c7046e-7e98-416f-bc9b-586a14989bb7_terseLabel_en-US" xlink:label="lab_dei_EntityAddressPostalZipCode" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Entity Address, Postal Zip Code</link:label>
    <link:label id="lab_dei_EntityAddressPostalZipCode_label_en-US" xlink:label="lab_dei_EntityAddressPostalZipCode" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Entity Address, Postal Zip Code</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_EntityAddressPostalZipCode" xlink:href="https://xbrl.sec.gov/dei/2022/dei-2022.xsd#dei_EntityAddressPostalZipCode"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_EntityAddressPostalZipCode" xlink:to="lab_dei_EntityAddressPostalZipCode" xlink:type="arc" order="1"/>
    <link:label id="lab_root_RealEstateExitCostsMember_5caa520a-9982-4e47-9fc4-5b2ef5e697ec_terseLabel_en-US" xlink:label="lab_root_RealEstateExitCostsMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Real estate exit costs</link:label>
    <link:label id="lab_root_RealEstateExitCostsMember_label_en-US" xlink:label="lab_root_RealEstateExitCostsMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Real Estate Exit Costs [Member]</link:label>
    <link:label id="lab_root_RealEstateExitCostsMember_documentation_en-US" xlink:label="lab_root_RealEstateExitCostsMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Real Estate Exit Costs</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_root_RealEstateExitCostsMember" xlink:href="root-20220930.xsd#root_RealEstateExitCostsMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_root_RealEstateExitCostsMember" xlink:to="lab_root_RealEstateExitCostsMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_PreferredStockSharesOutstanding_ba4e7161-fa12-4b0b-a485-d91749a54673_terseLabel_en-US" xlink:label="lab_us-gaap_PreferredStockSharesOutstanding" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Preferred stock, shares outstanding (in shares)</link:label>
    <link:label id="lab_us-gaap_PreferredStockSharesOutstanding_label_en-US" xlink:label="lab_us-gaap_PreferredStockSharesOutstanding" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Preferred Stock, Shares Outstanding</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PreferredStockSharesOutstanding" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_PreferredStockSharesOutstanding"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PreferredStockSharesOutstanding" xlink:to="lab_us-gaap_PreferredStockSharesOutstanding" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ScheduleOfLiabilityForUnpaidClaimsAndClaimsAdjustmentExpense_57a830bc-c534-4f5e-aeb4-678a92c2f583_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfLiabilityForUnpaidClaimsAndClaimsAdjustmentExpense" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Schedule of Reconciliation of Reserve Balances for Loss and LAE, Net of Reinsurance</link:label>
    <link:label id="lab_us-gaap_ScheduleOfLiabilityForUnpaidClaimsAndClaimsAdjustmentExpense_label_en-US" xlink:label="lab_us-gaap_ScheduleOfLiabilityForUnpaidClaimsAndClaimsAdjustmentExpense" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Schedule of Liability for Unpaid Claims and Claims Adjustment Expense [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfLiabilityForUnpaidClaimsAndClaimsAdjustmentExpense" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ScheduleOfLiabilityForUnpaidClaimsAndClaimsAdjustmentExpense"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ScheduleOfLiabilityForUnpaidClaimsAndClaimsAdjustmentExpense" xlink:to="lab_us-gaap_ScheduleOfLiabilityForUnpaidClaimsAndClaimsAdjustmentExpense" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_GainLossOnInvestments_ed050bd6-2ba9-4eab-85fe-d9153539d149_terseLabel_en-US" xlink:label="lab_us-gaap_GainLossOnInvestments" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Net realized gains on investments</link:label>
    <link:label id="lab_us-gaap_GainLossOnInvestments_label_en-US" xlink:label="lab_us-gaap_GainLossOnInvestments" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Gain (Loss) on Investments</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_GainLossOnInvestments" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_GainLossOnInvestments"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_GainLossOnInvestments" xlink:to="lab_us-gaap_GainLossOnInvestments" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DebtInstrumentAxis_5ffabaff-b0e2-49d5-bb2e-2044ef2db52b_terseLabel_en-US" xlink:label="lab_us-gaap_DebtInstrumentAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt Instrument [Axis]</link:label>
    <link:label id="lab_us-gaap_DebtInstrumentAxis_label_en-US" xlink:label="lab_us-gaap_DebtInstrumentAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt Instrument [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtInstrumentAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_DebtInstrumentAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DebtInstrumentAxis" xlink:to="lab_us-gaap_DebtInstrumentAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_IncomeTaxDisclosureAbstract_7132e87e-a506-470b-be26-3e7be830ea83_terseLabel_en-US" xlink:label="lab_us-gaap_IncomeTaxDisclosureAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Income Tax Disclosure [Abstract]</link:label>
    <link:label id="lab_us-gaap_IncomeTaxDisclosureAbstract_label_en-US" xlink:label="lab_us-gaap_IncomeTaxDisclosureAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Income Tax Disclosure [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncomeTaxDisclosureAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_IncomeTaxDisclosureAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IncomeTaxDisclosureAbstract" xlink:to="lab_us-gaap_IncomeTaxDisclosureAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_InvestmentTextBlock_5d34aa36-2b20-4b49-9714-31dc5ef00d4b_terseLabel_en-US" xlink:label="lab_us-gaap_InvestmentTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">INVESTMENTS</link:label>
    <link:label id="lab_us-gaap_InvestmentTextBlock_label_en-US" xlink:label="lab_us-gaap_InvestmentTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Investment [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_InvestmentTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_InvestmentTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_InvestmentTextBlock" xlink:to="lab_us-gaap_InvestmentTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AdditionalPaidInCapital_b63a5c41-e9d2-474a-9580-a2b6500cc16b_terseLabel_en-US" xlink:label="lab_us-gaap_AdditionalPaidInCapital" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Additional paid-in capital</link:label>
    <link:label id="lab_us-gaap_AdditionalPaidInCapital_label_en-US" xlink:label="lab_us-gaap_AdditionalPaidInCapital" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Additional Paid in Capital</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AdditionalPaidInCapital" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_AdditionalPaidInCapital"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AdditionalPaidInCapital" xlink:to="lab_us-gaap_AdditionalPaidInCapital" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LiabilityForClaimsAndClaimsAdjustmentExpense_8816a633-6d3c-4ba6-9033-c8797e00c9a3_periodStartLabel_en-US" xlink:label="lab_us-gaap_LiabilityForClaimsAndClaimsAdjustmentExpense" xlink:role="http://www.xbrl.org/2003/role/periodStartLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Gross loss and LAE reserves, January 1</link:label>
    <link:label id="lab_us-gaap_LiabilityForClaimsAndClaimsAdjustmentExpense_6c703aa3-71bf-45ac-8988-e9a2014b5e39_periodEndLabel_en-US" xlink:label="lab_us-gaap_LiabilityForClaimsAndClaimsAdjustmentExpense" xlink:role="http://www.xbrl.org/2003/role/periodEndLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Gross loss and LAE reserves, September 30</link:label>
    <link:label id="lab_us-gaap_LiabilityForClaimsAndClaimsAdjustmentExpense_label_en-US" xlink:label="lab_us-gaap_LiabilityForClaimsAndClaimsAdjustmentExpense" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Liability for Claims and Claims Adjustment Expense</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LiabilityForClaimsAndClaimsAdjustmentExpense" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_LiabilityForClaimsAndClaimsAdjustmentExpense"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LiabilityForClaimsAndClaimsAdjustmentExpense" xlink:to="lab_us-gaap_LiabilityForClaimsAndClaimsAdjustmentExpense" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterFiveThroughTenYearsFairValue_377302c2-dd0a-43cf-944f-d7b32684e7b1_terseLabel_en-US" xlink:label="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterFiveThroughTenYearsFairValue" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Due five years through 10 years</link:label>
    <link:label id="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterFiveThroughTenYearsFairValue_label_en-US" xlink:label="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterFiveThroughTenYearsFairValue" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt Securities, Available-for-Sale, Fair Value, Maturity, Allocated and Single Maturity Date, after Year 5 Through 10</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterFiveThroughTenYearsFairValue" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterFiveThroughTenYearsFairValue"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterFiveThroughTenYearsFairValue" xlink:to="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterFiveThroughTenYearsFairValue" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FairValueDisclosureItemAmountsDomain_adbc0ce9-78fe-4d67-8d39-d4e67ca8bca8_terseLabel_en-US" xlink:label="lab_us-gaap_FairValueDisclosureItemAmountsDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Fair Value Measurement [Domain]</link:label>
    <link:label id="lab_us-gaap_FairValueDisclosureItemAmountsDomain_label_en-US" xlink:label="lab_us-gaap_FairValueDisclosureItemAmountsDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Fair Value Measurement [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueDisclosureItemAmountsDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_FairValueDisclosureItemAmountsDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FairValueDisclosureItemAmountsDomain" xlink:to="lab_us-gaap_FairValueDisclosureItemAmountsDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_TransfersAndServicingOfFinancialInstrumentsTypesOfFinancialInstrumentsDomain_3bfb3996-69be-4fa6-8f80-01929ac674c0_terseLabel_en-US" xlink:label="lab_us-gaap_TransfersAndServicingOfFinancialInstrumentsTypesOfFinancialInstrumentsDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Financial Instruments [Domain]</link:label>
    <link:label id="lab_us-gaap_TransfersAndServicingOfFinancialInstrumentsTypesOfFinancialInstrumentsDomain_label_en-US" xlink:label="lab_us-gaap_TransfersAndServicingOfFinancialInstrumentsTypesOfFinancialInstrumentsDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Financial Instruments [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_TransfersAndServicingOfFinancialInstrumentsTypesOfFinancialInstrumentsDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_TransfersAndServicingOfFinancialInstrumentsTypesOfFinancialInstrumentsDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_TransfersAndServicingOfFinancialInstrumentsTypesOfFinancialInstrumentsDomain" xlink:to="lab_us-gaap_TransfersAndServicingOfFinancialInstrumentsTypesOfFinancialInstrumentsDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DebtInstrumentBasisSpreadOnVariableRate1_01de3b31-c07f-401f-b092-cc88db23c018_terseLabel_en-US" xlink:label="lab_us-gaap_DebtInstrumentBasisSpreadOnVariableRate1" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Variable rate percentage (in percent)</link:label>
    <link:label id="lab_us-gaap_DebtInstrumentBasisSpreadOnVariableRate1_label_en-US" xlink:label="lab_us-gaap_DebtInstrumentBasisSpreadOnVariableRate1" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt Instrument, Basis Spread on Variable Rate</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtInstrumentBasisSpreadOnVariableRate1" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_DebtInstrumentBasisSpreadOnVariableRate1"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DebtInstrumentBasisSpreadOnVariableRate1" xlink:to="lab_us-gaap_DebtInstrumentBasisSpreadOnVariableRate1" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AvailableForSaleSecuritiesContinuousUnrealizedLossPositionFairValueAbstract_f7669a6e-b35f-4667-9fcf-c84b66952c4d_terseLabel_en-US" xlink:label="lab_us-gaap_AvailableForSaleSecuritiesContinuousUnrealizedLossPositionFairValueAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt Securities, Available-for-sale, Unrealized Loss Position [Line Items]</link:label>
    <link:label id="lab_us-gaap_AvailableForSaleSecuritiesContinuousUnrealizedLossPositionFairValueAbstract_label_en-US" xlink:label="lab_us-gaap_AvailableForSaleSecuritiesContinuousUnrealizedLossPositionFairValueAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt Securities, Available-for-Sale, Unrealized Loss Position [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AvailableForSaleSecuritiesContinuousUnrealizedLossPositionFairValueAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_AvailableForSaleSecuritiesContinuousUnrealizedLossPositionFairValueAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AvailableForSaleSecuritiesContinuousUnrealizedLossPositionFairValueAbstract" xlink:to="lab_us-gaap_AvailableForSaleSecuritiesContinuousUnrealizedLossPositionFairValueAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_RangeMember_b85bdfc2-39aa-455f-b6b7-bf2fbd48fdcd_terseLabel_en-US" xlink:label="lab_srt_RangeMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Statistical Measurement [Domain]</link:label>
    <link:label id="lab_srt_RangeMember_label_en-US" xlink:label="lab_srt_RangeMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Statistical Measurement [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_RangeMember" xlink:href="https://xbrl.fasb.org/srt/2022/elts/srt-2022.xsd#srt_RangeMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_RangeMember" xlink:to="lab_srt_RangeMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ProceedsFromIssuanceOfDebt_19fdc849-667d-4eeb-8457-910c609dbe67_terseLabel_en-US" xlink:label="lab_us-gaap_ProceedsFromIssuanceOfDebt" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Proceeds from issuance of debt and related warrants</link:label>
    <link:label id="lab_us-gaap_ProceedsFromIssuanceOfDebt_label_en-US" xlink:label="lab_us-gaap_ProceedsFromIssuanceOfDebt" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Proceeds from Issuance of Debt</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ProceedsFromIssuanceOfDebt" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ProceedsFromIssuanceOfDebt"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ProceedsFromIssuanceOfDebt" xlink:to="lab_us-gaap_ProceedsFromIssuanceOfDebt" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_StockIssuedDuringPeriodSharesStockOptionsExercised_63d9915e-e248-4721-8820-41d16c30741d_terseLabel_en-US" xlink:label="lab_us-gaap_StockIssuedDuringPeriodSharesStockOptionsExercised" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Common stock&#8212;option exercises and restricted stock units vesting, net of shares withheld for employee taxes (in shares)</link:label>
    <link:label id="lab_us-gaap_StockIssuedDuringPeriodSharesStockOptionsExercised_be763dc2-e7a2-4497-9940-ea009d934ea9_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_StockIssuedDuringPeriodSharesStockOptionsExercised" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Exercised (in shares)</link:label>
    <link:label id="lab_us-gaap_StockIssuedDuringPeriodSharesStockOptionsExercised_label_en-US" xlink:label="lab_us-gaap_StockIssuedDuringPeriodSharesStockOptionsExercised" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Share-Based Compensation Arrangement by Share-Based Payment Award, Options, Exercises in Period</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_StockIssuedDuringPeriodSharesStockOptionsExercised" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_StockIssuedDuringPeriodSharesStockOptionsExercised"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_StockIssuedDuringPeriodSharesStockOptionsExercised" xlink:to="lab_us-gaap_StockIssuedDuringPeriodSharesStockOptionsExercised" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DebtInstrumentInterestRateStatedPercentage_1058cbfd-3246-4d90-bd66-f09aacf47d04_terseLabel_en-US" xlink:label="lab_us-gaap_DebtInstrumentInterestRateStatedPercentage" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Stated percentage (in percent)</link:label>
    <link:label id="lab_us-gaap_DebtInstrumentInterestRateStatedPercentage_label_en-US" xlink:label="lab_us-gaap_DebtInstrumentInterestRateStatedPercentage" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt Instrument, Interest Rate, Stated Percentage</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtInstrumentInterestRateStatedPercentage" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_DebtInstrumentInterestRateStatedPercentage"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DebtInstrumentInterestRateStatedPercentage" xlink:to="lab_us-gaap_DebtInstrumentInterestRateStatedPercentage" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DisclosureOfCompensationRelatedCostsSharebasedPaymentsAbstract_label_en-US" xlink:label="lab_us-gaap_DisclosureOfCompensationRelatedCostsSharebasedPaymentsAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Share-Based Payment Arrangement [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DisclosureOfCompensationRelatedCostsSharebasedPaymentsAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_DisclosureOfCompensationRelatedCostsSharebasedPaymentsAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DisclosureOfCompensationRelatedCostsSharebasedPaymentsAbstract" xlink:to="lab_us-gaap_DisclosureOfCompensationRelatedCostsSharebasedPaymentsAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_StockIssuedDuringPeriodValueConversionOfConvertibleSecurities_138b0990-0c8c-47d4-a44a-86383479c242_terseLabel_en-US" xlink:label="lab_us-gaap_StockIssuedDuringPeriodValueConversionOfConvertibleSecurities" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Conversion of Class B to Class A</link:label>
    <link:label id="lab_us-gaap_StockIssuedDuringPeriodValueConversionOfConvertibleSecurities_label_en-US" xlink:label="lab_us-gaap_StockIssuedDuringPeriodValueConversionOfConvertibleSecurities" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Stock Issued During Period, Value, Conversion of Convertible Securities</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_StockIssuedDuringPeriodValueConversionOfConvertibleSecurities" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_StockIssuedDuringPeriodValueConversionOfConvertibleSecurities"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_StockIssuedDuringPeriodValueConversionOfConvertibleSecurities" xlink:to="lab_us-gaap_StockIssuedDuringPeriodValueConversionOfConvertibleSecurities" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_TemporaryEquitySharesOutstanding_f5b041a3-5250-4a42-95da-18b7eb91841c_periodStartLabel_en-US" xlink:label="lab_us-gaap_TemporaryEquitySharesOutstanding" xlink:role="http://www.xbrl.org/2003/role/periodStartLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Beginning balance (in shares)</link:label>
    <link:label id="lab_us-gaap_TemporaryEquitySharesOutstanding_d234c5d2-f0b0-4af1-ad9c-f7711490442c_periodEndLabel_en-US" xlink:label="lab_us-gaap_TemporaryEquitySharesOutstanding" xlink:role="http://www.xbrl.org/2003/role/periodEndLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Ending balance (in shares)</link:label>
    <link:label id="lab_us-gaap_TemporaryEquitySharesOutstanding_label_en-US" xlink:label="lab_us-gaap_TemporaryEquitySharesOutstanding" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Temporary Equity, Shares Outstanding</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_TemporaryEquitySharesOutstanding" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_TemporaryEquitySharesOutstanding"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_TemporaryEquitySharesOutstanding" xlink:to="lab_us-gaap_TemporaryEquitySharesOutstanding" xlink:type="arc" order="1"/>
    <link:label id="lab_root_LongTermWarrantMember_e0bfa4e2-3689-4f29-896d-7bd38ab7790b_terseLabel_en-US" xlink:label="lab_root_LongTermWarrantMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Long Term Warrant</link:label>
    <link:label id="lab_root_LongTermWarrantMember_label_en-US" xlink:label="lab_root_LongTermWarrantMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Long Term Warrant [Member]</link:label>
    <link:label id="lab_root_LongTermWarrantMember_documentation_en-US" xlink:label="lab_root_LongTermWarrantMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Long Term Warrant</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_root_LongTermWarrantMember" xlink:href="root-20220930.xsd#root_LongTermWarrantMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_root_LongTermWarrantMember" xlink:to="lab_root_LongTermWarrantMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_NetIncomeLoss_7b484174-95e0-4f0a-8c1a-5be7ac5c40b2_totalLabel_en-US" xlink:label="lab_us-gaap_NetIncomeLoss" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Net loss</link:label>
    <link:label id="lab_us-gaap_NetIncomeLoss_de5fd301-f8bd-4892-ab53-0119450880c3_terseLabel_en-US" xlink:label="lab_us-gaap_NetIncomeLoss" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Net loss</link:label>
    <link:label id="lab_us-gaap_NetIncomeLoss_70517969-5694-40d6-9fb6-5bbedcee078d_verboseLabel_en-US" xlink:label="lab_us-gaap_NetIncomeLoss" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Net loss</link:label>
    <link:label id="lab_us-gaap_NetIncomeLoss_label_en-US" xlink:label="lab_us-gaap_NetIncomeLoss" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Net Income (Loss) Attributable to Parent</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NetIncomeLoss" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_NetIncomeLoss"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_NetIncomeLoss" xlink:to="lab_us-gaap_NetIncomeLoss" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareLineItems_6749102e-e1f8-4333-9428-ce4c7f196385_terseLabel_en-US" xlink:label="lab_us-gaap_AntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareLineItems" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Antidilutive Securities Excluded from Computation of Earnings Per Share [Line Items]</link:label>
    <link:label id="lab_us-gaap_AntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareLineItems_label_en-US" xlink:label="lab_us-gaap_AntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Antidilutive Securities Excluded from Computation of Earnings Per Share [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareLineItems" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_AntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareLineItems"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareLineItems" xlink:to="lab_us-gaap_AntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareLineItems" xlink:type="arc" order="1"/>
    <link:label id="lab_root_SeriesAConvertiblePreferredStockMember_4e97c5a5-8be9-450c-a1dd-8e40346a961e_terseLabel_en-US" xlink:label="lab_root_SeriesAConvertiblePreferredStockMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Series A Convertible Preferred Stock</link:label>
    <link:label id="lab_root_SeriesAConvertiblePreferredStockMember_label_en-US" xlink:label="lab_root_SeriesAConvertiblePreferredStockMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Series A Convertible Preferred Stock [Member]</link:label>
    <link:label id="lab_root_SeriesAConvertiblePreferredStockMember_documentation_en-US" xlink:label="lab_root_SeriesAConvertiblePreferredStockMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Series A Convertible Preferred Stock</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_root_SeriesAConvertiblePreferredStockMember" xlink:href="root-20220930.xsd#root_SeriesAConvertiblePreferredStockMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_root_SeriesAConvertiblePreferredStockMember" xlink:to="lab_root_SeriesAConvertiblePreferredStockMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareAmount_ee799a00-66a1-4452-b8b2-247f022a317c_terseLabel_en-US" xlink:label="lab_us-gaap_AntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareAmount" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Anti-dilutive securities (in shares)</link:label>
    <link:label id="lab_us-gaap_AntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareAmount_label_en-US" xlink:label="lab_us-gaap_AntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareAmount" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Antidilutive Securities Excluded from Computation of Earnings Per Share, Amount</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareAmount" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_AntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareAmount"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareAmount" xlink:to="lab_us-gaap_AntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareAmount" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterOneThroughFiveYearsFairValue_c30999e4-d361-4ac3-8945-d951b7d7f40a_terseLabel_en-US" xlink:label="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterOneThroughFiveYearsFairValue" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Due after one year through five years</link:label>
    <link:label id="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterOneThroughFiveYearsFairValue_label_en-US" xlink:label="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterOneThroughFiveYearsFairValue" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt Securities, Available-for-Sale, Fair Value, Maturity, Allocated and Single Maturity Date, after Year One Through Five</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterOneThroughFiveYearsFairValue" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterOneThroughFiveYearsFairValue"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterOneThroughFiveYearsFairValue" xlink:to="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterOneThroughFiveYearsFairValue" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_SubsequentEventTypeAxis_72e90444-877d-435c-96d6-9a1d5d5ad4c2_terseLabel_en-US" xlink:label="lab_us-gaap_SubsequentEventTypeAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Subsequent Event Type [Axis]</link:label>
    <link:label id="lab_us-gaap_SubsequentEventTypeAxis_label_en-US" xlink:label="lab_us-gaap_SubsequentEventTypeAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Subsequent Event Type [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SubsequentEventTypeAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_SubsequentEventTypeAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_SubsequentEventTypeAxis" xlink:to="lab_us-gaap_SubsequentEventTypeAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_root_ShareBasedCompensationAwardTrancheFourMember_6258df32-bd0f-4364-923e-2a527423081d_terseLabel_en-US" xlink:label="lab_root_ShareBasedCompensationAwardTrancheFourMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Tranche 4</link:label>
    <link:label id="lab_root_ShareBasedCompensationAwardTrancheFourMember_label_en-US" xlink:label="lab_root_ShareBasedCompensationAwardTrancheFourMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Share Based Compensation Award Tranche Four [Member]</link:label>
    <link:label id="lab_root_ShareBasedCompensationAwardTrancheFourMember_documentation_en-US" xlink:label="lab_root_ShareBasedCompensationAwardTrancheFourMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Share Based Compensation Award Tranche Four</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_root_ShareBasedCompensationAwardTrancheFourMember" xlink:href="root-20220930.xsd#root_ShareBasedCompensationAwardTrancheFourMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_root_ShareBasedCompensationAwardTrancheFourMember" xlink:to="lab_root_ShareBasedCompensationAwardTrancheFourMember" xlink:type="arc" order="1"/>
    <link:label id="lab_root_DebtInstrumentFloorInterestRate_f8f0df18-6c33-444f-aeab-56323a87a251_terseLabel_en-US" xlink:label="lab_root_DebtInstrumentFloorInterestRate" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt instrument, floor interest rate (in percent)</link:label>
    <link:label id="lab_root_DebtInstrumentFloorInterestRate_label_en-US" xlink:label="lab_root_DebtInstrumentFloorInterestRate" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt Instrument, Floor Interest Rate</link:label>
    <link:label id="lab_root_DebtInstrumentFloorInterestRate_documentation_en-US" xlink:label="lab_root_DebtInstrumentFloorInterestRate" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt Instrument, Floor Interest Rate</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_root_DebtInstrumentFloorInterestRate" xlink:href="root-20220930.xsd#root_DebtInstrumentFloorInterestRate"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_root_DebtInstrumentFloorInterestRate" xlink:to="lab_root_DebtInstrumentFloorInterestRate" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_NetInvestmentIncome_c44d3065-b0a9-46d7-a7fc-cdede57db4d8_terseLabel_en-US" xlink:label="lab_us-gaap_NetInvestmentIncome" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Net investment income</link:label>
    <link:label id="lab_us-gaap_NetInvestmentIncome_39b470dc-22a3-4a24-86d0-c85d80d7c469_totalLabel_en-US" xlink:label="lab_us-gaap_NetInvestmentIncome" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Net investment income</link:label>
    <link:label id="lab_us-gaap_NetInvestmentIncome_label_en-US" xlink:label="lab_us-gaap_NetInvestmentIncome" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Net Investment Income</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NetInvestmentIncome" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_NetInvestmentIncome"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_NetInvestmentIncome" xlink:to="lab_us-gaap_NetInvestmentIncome" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EquityComponentDomain_5dcec574-0ae2-4230-876c-84b2613faf2e_terseLabel_en-US" xlink:label="lab_us-gaap_EquityComponentDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Equity Component [Domain]</link:label>
    <link:label id="lab_us-gaap_EquityComponentDomain_label_en-US" xlink:label="lab_us-gaap_EquityComponentDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Equity Component [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EquityComponentDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_EquityComponentDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EquityComponentDomain" xlink:to="lab_us-gaap_EquityComponentDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_SubsequentEventTypeDomain_1f7265d0-73e3-4e7a-a8e8-9b3d90f226c2_terseLabel_en-US" xlink:label="lab_us-gaap_SubsequentEventTypeDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Subsequent Event Type [Domain]</link:label>
    <link:label id="lab_us-gaap_SubsequentEventTypeDomain_label_en-US" xlink:label="lab_us-gaap_SubsequentEventTypeDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Subsequent Event Type [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SubsequentEventTypeDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_SubsequentEventTypeDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_SubsequentEventTypeDomain" xlink:to="lab_us-gaap_SubsequentEventTypeDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_root_OtherInsuranceExpenseBenefitMember_4e7b6476-4b87-4da8-935e-a68ad3d6964a_terseLabel_en-US" xlink:label="lab_root_OtherInsuranceExpenseBenefitMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Other insurance expense (benefit)</link:label>
    <link:label id="lab_root_OtherInsuranceExpenseBenefitMember_label_en-US" xlink:label="lab_root_OtherInsuranceExpenseBenefitMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Other Insurance Expense (Benefit) [Member]</link:label>
    <link:label id="lab_root_OtherInsuranceExpenseBenefitMember_documentation_en-US" xlink:label="lab_root_OtherInsuranceExpenseBenefitMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Other Insurance Expense (Benefit)</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_root_OtherInsuranceExpenseBenefitMember" xlink:href="root-20220930.xsd#root_OtherInsuranceExpenseBenefitMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_root_OtherInsuranceExpenseBenefitMember" xlink:to="lab_root_OtherInsuranceExpenseBenefitMember" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_StatementScenarioAxis_2c60ab14-58b7-425d-b360-b6c0a10f82fb_terseLabel_en-US" xlink:label="lab_srt_StatementScenarioAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Scenario [Axis]</link:label>
    <link:label id="lab_srt_StatementScenarioAxis_label_en-US" xlink:label="lab_srt_StatementScenarioAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Scenario [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_StatementScenarioAxis" xlink:href="https://xbrl.fasb.org/srt/2022/elts/srt-2022.xsd#srt_StatementScenarioAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_StatementScenarioAxis" xlink:to="lab_srt_StatementScenarioAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_SecuredDebtMember_ee1dc644-3e95-4ccd-a9c8-d864e7d645f5_terseLabel_en-US" xlink:label="lab_us-gaap_SecuredDebtMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Secured debt</link:label>
    <link:label id="lab_us-gaap_SecuredDebtMember_label_en-US" xlink:label="lab_us-gaap_SecuredDebtMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Secured Debt [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SecuredDebtMember" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_SecuredDebtMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_SecuredDebtMember" xlink:to="lab_us-gaap_SecuredDebtMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseNetAbstract_62a94b92-4db9-484f-a4b9-f113a32aaf27_terseLabel_en-US" xlink:label="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseNetAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Liability for Unpaid Claims and Claims Adjustment Expense [Roll Forward]</link:label>
    <link:label id="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseNetAbstract_label_en-US" xlink:label="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseNetAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Liability for Unpaid Claims and Claims Adjustment Expense [Roll Forward]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseNetAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseNetAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseNetAbstract" xlink:to="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseNetAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AssetsFairValueDisclosure_aa9da0b3-d406-4c4a-93f9-959fbdca34ed_totalLabel_en-US" xlink:label="lab_us-gaap_AssetsFairValueDisclosure" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Total assets at fair value</link:label>
    <link:label id="lab_us-gaap_AssetsFairValueDisclosure_label_en-US" xlink:label="lab_us-gaap_AssetsFairValueDisclosure" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Assets, Fair Value Disclosure</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AssetsFairValueDisclosure" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_AssetsFairValueDisclosure"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AssetsFairValueDisclosure" xlink:to="lab_us-gaap_AssetsFairValueDisclosure" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_RestructuringPlanAxis_6c5b5206-c01d-4b35-9ec2-f63e971d88fb_terseLabel_en-US" xlink:label="lab_us-gaap_RestructuringPlanAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Restructuring Plan [Axis]</link:label>
    <link:label id="lab_us-gaap_RestructuringPlanAxis_label_en-US" xlink:label="lab_us-gaap_RestructuringPlanAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Restructuring Plan [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_RestructuringPlanAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_RestructuringPlanAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_RestructuringPlanAxis" xlink:to="lab_us-gaap_RestructuringPlanAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_EquityMethodInvesteeNameDomain_1e34369b-9988-4a48-9d76-2d3c5b70d42a_terseLabel_en-US" xlink:label="lab_srt_EquityMethodInvesteeNameDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Investment, Name [Domain]</link:label>
    <link:label id="lab_srt_EquityMethodInvesteeNameDomain_label_en-US" xlink:label="lab_srt_EquityMethodInvesteeNameDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Investment, Name [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_EquityMethodInvesteeNameDomain" xlink:href="https://xbrl.fasb.org/srt/2022/elts/srt-2022.xsd#srt_EquityMethodInvesteeNameDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_EquityMethodInvesteeNameDomain" xlink:to="lab_srt_EquityMethodInvesteeNameDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_root_APICShareBasedPaymentArrangementIncreaseForCostRecognitionWarrants_ecb15675-1537-4c44-b5d7-4eca1115fe51_terseLabel_en-US" xlink:label="lab_root_APICShareBasedPaymentArrangementIncreaseForCostRecognitionWarrants" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Warrant compensation expense</link:label>
    <link:label id="lab_root_APICShareBasedPaymentArrangementIncreaseForCostRecognitionWarrants_label_en-US" xlink:label="lab_root_APICShareBasedPaymentArrangementIncreaseForCostRecognitionWarrants" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">APIC, Share-based Payment Arrangement, Increase for Cost Recognition, Warrants</link:label>
    <link:label id="lab_root_APICShareBasedPaymentArrangementIncreaseForCostRecognitionWarrants_documentation_en-US" xlink:label="lab_root_APICShareBasedPaymentArrangementIncreaseForCostRecognitionWarrants" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">APIC, Share-based Payment Arrangement, Increase for Cost Recognition, Warrants</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_root_APICShareBasedPaymentArrangementIncreaseForCostRecognitionWarrants" xlink:href="root-20220930.xsd#root_APICShareBasedPaymentArrangementIncreaseForCostRecognitionWarrants"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_root_APICShareBasedPaymentArrangementIncreaseForCostRecognitionWarrants" xlink:to="lab_root_APICShareBasedPaymentArrangementIncreaseForCostRecognitionWarrants" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_PlanNameAxis_e36f1d7a-17ed-43a2-b655-fcc05b89b341_terseLabel_en-US" xlink:label="lab_us-gaap_PlanNameAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Plan Name [Axis]</link:label>
    <link:label id="lab_us-gaap_PlanNameAxis_label_en-US" xlink:label="lab_us-gaap_PlanNameAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Plan Name [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PlanNameAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_PlanNameAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PlanNameAxis" xlink:to="lab_us-gaap_PlanNameAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AvailableForSaleSecuritiesDebtSecurities_e5da02d2-a0a7-462e-9f76-80fce898655d_terseLabel_en-US" xlink:label="lab_us-gaap_AvailableForSaleSecuritiesDebtSecurities" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Fair Value</link:label>
    <link:label id="lab_us-gaap_AvailableForSaleSecuritiesDebtSecurities_2cc1eb0d-f915-4952-ab9a-1f722a5444b6_totalLabel_en-US" xlink:label="lab_us-gaap_AvailableForSaleSecuritiesDebtSecurities" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Total</link:label>
    <link:label id="lab_us-gaap_AvailableForSaleSecuritiesDebtSecurities_293e34e9-0710-4b60-ad5f-c7b577847e91_verboseLabel_en-US" xlink:label="lab_us-gaap_AvailableForSaleSecuritiesDebtSecurities" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">AFS securities</link:label>
    <link:label id="lab_us-gaap_AvailableForSaleSecuritiesDebtSecurities_label_en-US" xlink:label="lab_us-gaap_AvailableForSaleSecuritiesDebtSecurities" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt Securities, Available-for-Sale</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AvailableForSaleSecuritiesDebtSecurities" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_AvailableForSaleSecuritiesDebtSecurities"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AvailableForSaleSecuritiesDebtSecurities" xlink:to="lab_us-gaap_AvailableForSaleSecuritiesDebtSecurities" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EmployeeServiceShareBasedCompensationNonvestedAwardsTotalCompensationCostNotYetRecognizedShareBasedAwardsOtherThanOptions_5ef8f1d6-c56c-490e-92e6-9bb9fc63f387_terseLabel_en-US" xlink:label="lab_us-gaap_EmployeeServiceShareBasedCompensationNonvestedAwardsTotalCompensationCostNotYetRecognizedShareBasedAwardsOtherThanOptions" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Unrecognized compensation cost</link:label>
    <link:label id="lab_us-gaap_EmployeeServiceShareBasedCompensationNonvestedAwardsTotalCompensationCostNotYetRecognizedShareBasedAwardsOtherThanOptions_label_en-US" xlink:label="lab_us-gaap_EmployeeServiceShareBasedCompensationNonvestedAwardsTotalCompensationCostNotYetRecognizedShareBasedAwardsOtherThanOptions" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Share-Based Payment Arrangement, Nonvested Award, Excluding Option, Cost Not yet Recognized, Amount</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EmployeeServiceShareBasedCompensationNonvestedAwardsTotalCompensationCostNotYetRecognizedShareBasedAwardsOtherThanOptions" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_EmployeeServiceShareBasedCompensationNonvestedAwardsTotalCompensationCostNotYetRecognizedShareBasedAwardsOtherThanOptions"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EmployeeServiceShareBasedCompensationNonvestedAwardsTotalCompensationCostNotYetRecognizedShareBasedAwardsOtherThanOptions" xlink:to="lab_us-gaap_EmployeeServiceShareBasedCompensationNonvestedAwardsTotalCompensationCostNotYetRecognizedShareBasedAwardsOtherThanOptions" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_PlanNameDomain_694aaa63-537a-4b03-a974-6daaf487eea9_terseLabel_en-US" xlink:label="lab_us-gaap_PlanNameDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Plan Name [Domain]</link:label>
    <link:label id="lab_us-gaap_PlanNameDomain_label_en-US" xlink:label="lab_us-gaap_PlanNameDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Plan Name [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PlanNameDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_PlanNameDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PlanNameDomain" xlink:to="lab_us-gaap_PlanNameDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ReinsurancePremiumsForInsuranceCompaniesByProductSegmentNetAmountAbstract_a52fd8e0-2167-4ff2-90b8-fe3cc4f8f2a4_terseLabel_en-US" xlink:label="lab_us-gaap_ReinsurancePremiumsForInsuranceCompaniesByProductSegmentNetAmountAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Premiums earned:</link:label>
    <link:label id="lab_us-gaap_ReinsurancePremiumsForInsuranceCompaniesByProductSegmentNetAmountAbstract_label_en-US" xlink:label="lab_us-gaap_ReinsurancePremiumsForInsuranceCompaniesByProductSegmentNetAmountAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Premiums Earned, Net [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ReinsurancePremiumsForInsuranceCompaniesByProductSegmentNetAmountAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ReinsurancePremiumsForInsuranceCompaniesByProductSegmentNetAmountAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ReinsurancePremiumsForInsuranceCompaniesByProductSegmentNetAmountAbstract" xlink:to="lab_us-gaap_ReinsurancePremiumsForInsuranceCompaniesByProductSegmentNetAmountAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_StatementOfCashFlowsAbstract_label_en-US" xlink:label="lab_us-gaap_StatementOfCashFlowsAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Statement of Cash Flows [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_StatementOfCashFlowsAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_StatementOfCashFlowsAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_StatementOfCashFlowsAbstract" xlink:to="lab_us-gaap_StatementOfCashFlowsAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_EntityAddressStateOrProvince_87452fb2-3220-4468-b83e-9a2a0f274f18_terseLabel_en-US" xlink:label="lab_dei_EntityAddressStateOrProvince" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Entity Address, State or Province</link:label>
    <link:label id="lab_dei_EntityAddressStateOrProvince_label_en-US" xlink:label="lab_dei_EntityAddressStateOrProvince" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Entity Address, State or Province</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_EntityAddressStateOrProvince" xlink:href="https://xbrl.sec.gov/dei/2022/dei-2022.xsd#dei_EntityAddressStateOrProvince"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_EntityAddressStateOrProvince" xlink:to="lab_dei_EntityAddressStateOrProvince" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FairValueInputsLevel1Member_4f581092-9b00-4ba2-9d1a-ee0020155b5a_terseLabel_en-US" xlink:label="lab_us-gaap_FairValueInputsLevel1Member" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Level 1</link:label>
    <link:label id="lab_us-gaap_FairValueInputsLevel1Member_label_en-US" xlink:label="lab_us-gaap_FairValueInputsLevel1Member" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Fair Value, Inputs, Level 1 [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueInputsLevel1Member" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_FairValueInputsLevel1Member"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FairValueInputsLevel1Member" xlink:to="lab_us-gaap_FairValueInputsLevel1Member" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_PrepaidReinsurancePremiums_d356ca6e-e44e-4c80-92a1-0fe9d22c8237_terseLabel_en-US" xlink:label="lab_us-gaap_PrepaidReinsurancePremiums" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Prepaid reinsurance premiums</link:label>
    <link:label id="lab_us-gaap_PrepaidReinsurancePremiums_label_en-US" xlink:label="lab_us-gaap_PrepaidReinsurancePremiums" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Prepaid Reinsurance Premiums</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PrepaidReinsurancePremiums" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_PrepaidReinsurancePremiums"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PrepaidReinsurancePremiums" xlink:to="lab_us-gaap_PrepaidReinsurancePremiums" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_SharebasedCompensationArrangementBySharebasedPaymentAwardOptionsOutstandingWeightedAverageRemainingContractualTerm2_270e35e6-8627-42b1-b45a-bb09d939395f_verboseLabel_en-US" xlink:label="lab_us-gaap_SharebasedCompensationArrangementBySharebasedPaymentAwardOptionsOutstandingWeightedAverageRemainingContractualTerm2" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Outstanding, weighted-average remaining contractual term (in years)</link:label>
    <link:label id="lab_us-gaap_SharebasedCompensationArrangementBySharebasedPaymentAwardOptionsOutstandingWeightedAverageRemainingContractualTerm2_label_en-US" xlink:label="lab_us-gaap_SharebasedCompensationArrangementBySharebasedPaymentAwardOptionsOutstandingWeightedAverageRemainingContractualTerm2" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Share-Based Compensation Arrangement by Share-Based Payment Award, Options, Outstanding, Weighted Average Remaining Contractual Term</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SharebasedCompensationArrangementBySharebasedPaymentAwardOptionsOutstandingWeightedAverageRemainingContractualTerm2" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_SharebasedCompensationArrangementBySharebasedPaymentAwardOptionsOutstandingWeightedAverageRemainingContractualTerm2"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_SharebasedCompensationArrangementBySharebasedPaymentAwardOptionsOutstandingWeightedAverageRemainingContractualTerm2" xlink:to="lab_us-gaap_SharebasedCompensationArrangementBySharebasedPaymentAwardOptionsOutstandingWeightedAverageRemainingContractualTerm2" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AdjustmentOfWarrantsGrantedForServices_d65fc510-a29c-469c-9299-4f96eec6b20d_terseLabel_en-US" xlink:label="lab_us-gaap_AdjustmentOfWarrantsGrantedForServices" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Warrant compensation expense</link:label>
    <link:label id="lab_us-gaap_AdjustmentOfWarrantsGrantedForServices_label_en-US" xlink:label="lab_us-gaap_AdjustmentOfWarrantsGrantedForServices" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Adjustment of Warrants Granted for Services</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AdjustmentOfWarrantsGrantedForServices" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_AdjustmentOfWarrantsGrantedForServices"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AdjustmentOfWarrantsGrantedForServices" xlink:to="lab_us-gaap_AdjustmentOfWarrantsGrantedForServices" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AwardTypeAxis_226bc58e-1961-4356-8b91-e2299fa66d1b_terseLabel_en-US" xlink:label="lab_us-gaap_AwardTypeAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Award Type [Axis]</link:label>
    <link:label id="lab_us-gaap_AwardTypeAxis_label_en-US" xlink:label="lab_us-gaap_AwardTypeAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Award Type [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AwardTypeAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_AwardTypeAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AwardTypeAxis" xlink:to="lab_us-gaap_AwardTypeAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_root_ClassOfWarrantsIssuedAndOutstandingSharesPercentage_90640150-bdbd-4cc8-a92e-beaa12d5a4f8_terseLabel_en-US" xlink:label="lab_root_ClassOfWarrantsIssuedAndOutstandingSharesPercentage" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Warrants issued and outstanding shares percentage (in percent)</link:label>
    <link:label id="lab_root_ClassOfWarrantsIssuedAndOutstandingSharesPercentage_label_en-US" xlink:label="lab_root_ClassOfWarrantsIssuedAndOutstandingSharesPercentage" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Class Of Warrants Issued And Outstanding Shares Percentage</link:label>
    <link:label id="lab_root_ClassOfWarrantsIssuedAndOutstandingSharesPercentage_documentation_en-US" xlink:label="lab_root_ClassOfWarrantsIssuedAndOutstandingSharesPercentage" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Class Of Warrants Issued And Outstanding Shares Percentage</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_root_ClassOfWarrantsIssuedAndOutstandingSharesPercentage" xlink:href="root-20220930.xsd#root_ClassOfWarrantsIssuedAndOutstandingSharesPercentage"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_root_ClassOfWarrantsIssuedAndOutstandingSharesPercentage" xlink:to="lab_root_ClassOfWarrantsIssuedAndOutstandingSharesPercentage" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_NetCashProvidedByUsedInOperatingActivities_d461c28c-b2c2-469f-b2df-d73ed87b82a4_totalLabel_en-US" xlink:label="lab_us-gaap_NetCashProvidedByUsedInOperatingActivities" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Net cash used in operating activities</link:label>
    <link:label id="lab_us-gaap_NetCashProvidedByUsedInOperatingActivities_label_en-US" xlink:label="lab_us-gaap_NetCashProvidedByUsedInOperatingActivities" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Net Cash Provided by (Used in) Operating Activities</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NetCashProvidedByUsedInOperatingActivities" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_NetCashProvidedByUsedInOperatingActivities"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_NetCashProvidedByUsedInOperatingActivities" xlink:to="lab_us-gaap_NetCashProvidedByUsedInOperatingActivities" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_RestructuringCosts_9338d218-3544-4f35-ac06-973fa9eed25b_terseLabel_en-US" xlink:label="lab_us-gaap_RestructuringCosts" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Total restructuring costs</link:label>
    <link:label id="lab_us-gaap_RestructuringCosts_label_en-US" xlink:label="lab_us-gaap_RestructuringCosts" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Restructuring Costs</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_RestructuringCosts" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_RestructuringCosts"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_RestructuringCosts" xlink:to="lab_us-gaap_RestructuringCosts" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ScheduleOfEmployeeServiceShareBasedCompensationAllocationOfRecognizedPeriodCostsTable_90965133-323a-4320-af3c-3eee471d356a_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfEmployeeServiceShareBasedCompensationAllocationOfRecognizedPeriodCostsTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Share-based Payment Arrangement, Expensed and Capitalized, Amount [Table]</link:label>
    <link:label id="lab_us-gaap_ScheduleOfEmployeeServiceShareBasedCompensationAllocationOfRecognizedPeriodCostsTable_label_en-US" xlink:label="lab_us-gaap_ScheduleOfEmployeeServiceShareBasedCompensationAllocationOfRecognizedPeriodCostsTable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Share-Based Payment Arrangement, Expensed and Capitalized, Amount [Table]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfEmployeeServiceShareBasedCompensationAllocationOfRecognizedPeriodCostsTable" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ScheduleOfEmployeeServiceShareBasedCompensationAllocationOfRecognizedPeriodCostsTable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ScheduleOfEmployeeServiceShareBasedCompensationAllocationOfRecognizedPeriodCostsTable" xlink:to="lab_us-gaap_ScheduleOfEmployeeServiceShareBasedCompensationAllocationOfRecognizedPeriodCostsTable" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleTableTextBlock_78732be3-d2be-4f76-9628-5ddf142ba3fe_terseLabel_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Schedule of AFS Debt Securities</link:label>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleTableTextBlock_label_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt Securities, Available-for-Sale [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtSecuritiesAvailableForSaleTableTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_DebtSecuritiesAvailableForSaleTableTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DebtSecuritiesAvailableForSaleTableTextBlock" xlink:to="lab_us-gaap_DebtSecuritiesAvailableForSaleTableTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_EntityListingsLineItems_694544e2-74f0-4240-af52-3de6f2830d31_terseLabel_en-US" xlink:label="lab_dei_EntityListingsLineItems" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Entity Listings [Line Items]</link:label>
    <link:label id="lab_dei_EntityListingsLineItems_label_en-US" xlink:label="lab_dei_EntityListingsLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Entity Listings [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_EntityListingsLineItems" xlink:href="https://xbrl.sec.gov/dei/2022/dei-2022.xsd#dei_EntityListingsLineItems"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_EntityListingsLineItems" xlink:to="lab_dei_EntityListingsLineItems" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_OtherLiabilities_cfb37073-64a8-4af9-8ef4-aa0f2aba835c_terseLabel_en-US" xlink:label="lab_us-gaap_OtherLiabilities" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Other liabilities</link:label>
    <link:label id="lab_us-gaap_OtherLiabilities_label_en-US" xlink:label="lab_us-gaap_OtherLiabilities" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Other Liabilities</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OtherLiabilities" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_OtherLiabilities"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_OtherLiabilities" xlink:to="lab_us-gaap_OtherLiabilities" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ScheduleOfAntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareTable_e39a73cb-a6bd-45c6-a2ce-f8b1b7fdd679_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfAntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Schedule of Antidilutive Securities Excluded from Computation of Earnings Per Share [Table]</link:label>
    <link:label id="lab_us-gaap_ScheduleOfAntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareTable_label_en-US" xlink:label="lab_us-gaap_ScheduleOfAntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareTable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Schedule of Antidilutive Securities Excluded from Computation of Earnings Per Share [Table]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfAntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareTable" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ScheduleOfAntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareTable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ScheduleOfAntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareTable" xlink:to="lab_us-gaap_ScheduleOfAntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareTable" xlink:type="arc" order="1"/>
    <link:label id="lab_root_WarrantsIssuedExercisePriceTradingDaysWeightedAveragePrice_e7971ba8-b99c-4598-8c78-82b4b6959a15_terseLabel_en-US" xlink:label="lab_root_WarrantsIssuedExercisePriceTradingDaysWeightedAveragePrice" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Trading days weighted average price</link:label>
    <link:label id="lab_root_WarrantsIssuedExercisePriceTradingDaysWeightedAveragePrice_label_en-US" xlink:label="lab_root_WarrantsIssuedExercisePriceTradingDaysWeightedAveragePrice" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Warrants Issued Exercise Price, Trading Days Weighted Average Price</link:label>
    <link:label id="lab_root_WarrantsIssuedExercisePriceTradingDaysWeightedAveragePrice_documentation_en-US" xlink:label="lab_root_WarrantsIssuedExercisePriceTradingDaysWeightedAveragePrice" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Warrants Issued Exercise Price, Trading Days Weighted Average Price</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_root_WarrantsIssuedExercisePriceTradingDaysWeightedAveragePrice" xlink:href="root-20220930.xsd#root_WarrantsIssuedExercisePriceTradingDaysWeightedAveragePrice"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_root_WarrantsIssuedExercisePriceTradingDaysWeightedAveragePrice" xlink:to="lab_root_WarrantsIssuedExercisePriceTradingDaysWeightedAveragePrice" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ScheduleOfEquityMethodInvestmentsLineItems_2022f272-e49b-4100-b9ae-2ffaa4b7eead_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfEquityMethodInvestmentsLineItems" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Schedule of Equity Method Investments [Line Items]</link:label>
    <link:label id="lab_us-gaap_ScheduleOfEquityMethodInvestmentsLineItems_label_en-US" xlink:label="lab_us-gaap_ScheduleOfEquityMethodInvestmentsLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Schedule of Equity Method Investments [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfEquityMethodInvestmentsLineItems" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ScheduleOfEquityMethodInvestmentsLineItems"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ScheduleOfEquityMethodInvestmentsLineItems" xlink:to="lab_us-gaap_ScheduleOfEquityMethodInvestmentsLineItems" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_Liabilities_e1aa5c00-f379-47a9-9957-c0498a57a797_totalLabel_en-US" xlink:label="lab_us-gaap_Liabilities" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Total liabilities</link:label>
    <link:label id="lab_us-gaap_Liabilities_label_en-US" xlink:label="lab_us-gaap_Liabilities" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Liabilities</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_Liabilities" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_Liabilities"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_Liabilities" xlink:to="lab_us-gaap_Liabilities" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_IncreaseDecreaseInUnearnedPremiums_0b20acd0-643b-4462-8702-0012bb392644_terseLabel_en-US" xlink:label="lab_us-gaap_IncreaseDecreaseInUnearnedPremiums" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Unearned premiums</link:label>
    <link:label id="lab_us-gaap_IncreaseDecreaseInUnearnedPremiums_label_en-US" xlink:label="lab_us-gaap_IncreaseDecreaseInUnearnedPremiums" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Increase (Decrease) in Unearned Premiums</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncreaseDecreaseInUnearnedPremiums" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_IncreaseDecreaseInUnearnedPremiums"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IncreaseDecreaseInUnearnedPremiums" xlink:to="lab_us-gaap_IncreaseDecreaseInUnearnedPremiums" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_StatementGeographicalAxis_dc000279-4dec-428b-99d6-7f2ee19c3051_terseLabel_en-US" xlink:label="lab_srt_StatementGeographicalAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Geographical [Axis]</link:label>
    <link:label id="lab_srt_StatementGeographicalAxis_label_en-US" xlink:label="lab_srt_StatementGeographicalAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Geographical [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_StatementGeographicalAxis" xlink:href="https://xbrl.fasb.org/srt/2022/elts/srt-2022.xsd#srt_StatementGeographicalAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_StatementGeographicalAxis" xlink:to="lab_srt_StatementGeographicalAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardLineItems_0ff93401-39ea-4b76-a516-91baa7c50af7_terseLabel_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardLineItems" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Share-based Compensation Arrangement by Share-based Payment Award [Line Items]</link:label>
    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardLineItems_label_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Share-Based Compensation Arrangement by Share-Based Payment Award [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardLineItems" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardLineItems"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardLineItems" xlink:to="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardLineItems" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_NetCashProvidedByUsedInInvestingActivitiesAbstract_62571b58-a960-4f4e-99e9-1b7917c28d08_terseLabel_en-US" xlink:label="lab_us-gaap_NetCashProvidedByUsedInInvestingActivitiesAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Cash flows from investing activities:</link:label>
    <link:label id="lab_us-gaap_NetCashProvidedByUsedInInvestingActivitiesAbstract_label_en-US" xlink:label="lab_us-gaap_NetCashProvidedByUsedInInvestingActivitiesAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Net Cash Provided by (Used in) Investing Activities [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NetCashProvidedByUsedInInvestingActivitiesAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_NetCashProvidedByUsedInInvestingActivitiesAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_NetCashProvidedByUsedInInvestingActivitiesAbstract" xlink:to="lab_us-gaap_NetCashProvidedByUsedInInvestingActivitiesAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidPriorYears1_4ffec55d-2afe-4983-8f0d-1fa344b7daec_terseLabel_en-US" xlink:label="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidPriorYears1" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Prior years</link:label>
    <link:label id="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidPriorYears1_label_en-US" xlink:label="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidPriorYears1" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Liability for Unpaid Claims and Claims Adjustment Expense, Claims Paid, Prior Years</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidPriorYears1" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidPriorYears1"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidPriorYears1" xlink:to="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidPriorYears1" xlink:type="arc" order="1"/>
    <link:label id="lab_root_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsGross_f28c7f23-558e-4d5a-aac6-98b8638ddfaf_terseLabel_en-US" xlink:label="lab_root_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsGross" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Direct</link:label>
    <link:label id="lab_root_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsGross_label_en-US" xlink:label="lab_root_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsGross" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Liability For Unpaid Claims And Claims Adjustment Expense, Incurred Claims, Gross</link:label>
    <link:label id="lab_root_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsGross_documentation_en-US" xlink:label="lab_root_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsGross" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Liability For Unpaid Claims And Claims Adjustment Expense, Incurred Claims, Gross</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_root_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsGross" xlink:href="root-20220930.xsd#root_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsGross"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_root_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsGross" xlink:to="lab_root_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsGross" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_IncreaseDecreaseInTemporaryEquityRollForward_64370ee7-9e7e-41ae-83fa-da6344d73f7d_terseLabel_en-US" xlink:label="lab_us-gaap_IncreaseDecreaseInTemporaryEquityRollForward" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Increase (Decrease) in Temporary Equity [Roll Forward]</link:label>
    <link:label id="lab_us-gaap_IncreaseDecreaseInTemporaryEquityRollForward_label_en-US" xlink:label="lab_us-gaap_IncreaseDecreaseInTemporaryEquityRollForward" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Increase (Decrease) in Temporary Equity [Roll Forward]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncreaseDecreaseInTemporaryEquityRollForward" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_IncreaseDecreaseInTemporaryEquityRollForward"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IncreaseDecreaseInTemporaryEquityRollForward" xlink:to="lab_us-gaap_IncreaseDecreaseInTemporaryEquityRollForward" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_SharebasedCompensationArrangementBySharebasedPaymentAwardEquityInstrumentsOtherThanOptionsAggregateIntrinsicValueVested_2b780b48-15fe-43cb-b23a-95142cd9e813_terseLabel_en-US" xlink:label="lab_us-gaap_SharebasedCompensationArrangementBySharebasedPaymentAwardEquityInstrumentsOtherThanOptionsAggregateIntrinsicValueVested" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Vested</link:label>
    <link:label id="lab_us-gaap_SharebasedCompensationArrangementBySharebasedPaymentAwardEquityInstrumentsOtherThanOptionsAggregateIntrinsicValueVested_label_en-US" xlink:label="lab_us-gaap_SharebasedCompensationArrangementBySharebasedPaymentAwardEquityInstrumentsOtherThanOptionsAggregateIntrinsicValueVested" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Share-Based Compensation Arrangement by Share-Based Payment Award, Equity Instruments Other than Options, Aggregate Intrinsic Value, Vested</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SharebasedCompensationArrangementBySharebasedPaymentAwardEquityInstrumentsOtherThanOptionsAggregateIntrinsicValueVested" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_SharebasedCompensationArrangementBySharebasedPaymentAwardEquityInstrumentsOtherThanOptionsAggregateIntrinsicValueVested"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_SharebasedCompensationArrangementBySharebasedPaymentAwardEquityInstrumentsOtherThanOptionsAggregateIntrinsicValueVested" xlink:to="lab_us-gaap_SharebasedCompensationArrangementBySharebasedPaymentAwardEquityInstrumentsOtherThanOptionsAggregateIntrinsicValueVested" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_EntityCommonStockSharesOutstanding_f8c232e3-bd45-42d2-bc68-5fdb3dd0cd7c_terseLabel_en-US" xlink:label="lab_dei_EntityCommonStockSharesOutstanding" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Entity Common Stock, Shares Outstanding</link:label>
    <link:label id="lab_dei_EntityCommonStockSharesOutstanding_label_en-US" xlink:label="lab_dei_EntityCommonStockSharesOutstanding" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Entity Common Stock, Shares Outstanding</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_EntityCommonStockSharesOutstanding" xlink:href="https://xbrl.sec.gov/dei/2022/dei-2022.xsd#dei_EntityCommonStockSharesOutstanding"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_EntityCommonStockSharesOutstanding" xlink:to="lab_dei_EntityCommonStockSharesOutstanding" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FairValueMeasurementsFairValueHierarchyDomain_f3a3bf3f-3f53-45e6-9c32-e5c8836e4ffa_terseLabel_en-US" xlink:label="lab_us-gaap_FairValueMeasurementsFairValueHierarchyDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Fair Value Hierarchy and NAV [Domain]</link:label>
    <link:label id="lab_us-gaap_FairValueMeasurementsFairValueHierarchyDomain_label_en-US" xlink:label="lab_us-gaap_FairValueMeasurementsFairValueHierarchyDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Fair Value Hierarchy and NAV [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueMeasurementsFairValueHierarchyDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_FairValueMeasurementsFairValueHierarchyDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FairValueMeasurementsFairValueHierarchyDomain" xlink:to="lab_us-gaap_FairValueMeasurementsFairValueHierarchyDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleAmortizedCostCurrent_047ca244-e281-43e3-b936-ab4e4cd8e40d_terseLabel_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleAmortizedCostCurrent" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Amortized cost, short term investments</link:label>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleAmortizedCostCurrent_label_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleAmortizedCostCurrent" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt Securities, Available-for-Sale, Amortized Cost, Current</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtSecuritiesAvailableForSaleAmortizedCostCurrent" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_DebtSecuritiesAvailableForSaleAmortizedCostCurrent"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DebtSecuritiesAvailableForSaleAmortizedCostCurrent" xlink:to="lab_us-gaap_DebtSecuritiesAvailableForSaleAmortizedCostCurrent" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ConversionOfStockSharesConverted1_e6e5a583-b281-40ba-8f47-b43ec455098b_terseLabel_en-US" xlink:label="lab_us-gaap_ConversionOfStockSharesConverted1" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Conversion of stock, shares converted</link:label>
    <link:label id="lab_us-gaap_ConversionOfStockSharesConverted1_label_en-US" xlink:label="lab_us-gaap_ConversionOfStockSharesConverted1" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Conversion of Stock, Shares Converted</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ConversionOfStockSharesConverted1" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ConversionOfStockSharesConverted1"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ConversionOfStockSharesConverted1" xlink:to="lab_us-gaap_ConversionOfStockSharesConverted1" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AvailableForSaleSecuritiesDebtSecuritiesCurrent_c9d9ccb7-8a40-495e-8203-5509116e64c2_terseLabel_en-US" xlink:label="lab_us-gaap_AvailableForSaleSecuritiesDebtSecuritiesCurrent" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Short-term investments (amortized cost: $0.4 and zero at September&#160;30, 2022 and December&#160;31, 2021, respectively)</link:label>
    <link:label id="lab_us-gaap_AvailableForSaleSecuritiesDebtSecuritiesCurrent_label_en-US" xlink:label="lab_us-gaap_AvailableForSaleSecuritiesDebtSecuritiesCurrent" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt Securities, Available-for-Sale, Current</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AvailableForSaleSecuritiesDebtSecuritiesCurrent" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_AvailableForSaleSecuritiesDebtSecuritiesCurrent"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AvailableForSaleSecuritiesDebtSecuritiesCurrent" xlink:to="lab_us-gaap_AvailableForSaleSecuritiesDebtSecuritiesCurrent" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_RestructuringAndRelatedCostNumberOfPositionsEliminated_0b32a3ea-d5d7-4457-be95-a52a23c1ea8d_terseLabel_en-US" xlink:label="lab_us-gaap_RestructuringAndRelatedCostNumberOfPositionsEliminated" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Workforce reduction</link:label>
    <link:label id="lab_us-gaap_RestructuringAndRelatedCostNumberOfPositionsEliminated_label_en-US" xlink:label="lab_us-gaap_RestructuringAndRelatedCostNumberOfPositionsEliminated" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Restructuring and Related Cost, Number of Positions Eliminated</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_RestructuringAndRelatedCostNumberOfPositionsEliminated" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_RestructuringAndRelatedCostNumberOfPositionsEliminated"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_RestructuringAndRelatedCostNumberOfPositionsEliminated" xlink:to="lab_us-gaap_RestructuringAndRelatedCostNumberOfPositionsEliminated" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AccumulatedNetUnrealizedInvestmentGainLossMember_bdee0803-71ab-4939-8e7b-67c226186243_terseLabel_en-US" xlink:label="lab_us-gaap_AccumulatedNetUnrealizedInvestmentGainLossMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Change in net unrealized gains (losses) on investments:</link:label>
    <link:label id="lab_us-gaap_AccumulatedNetUnrealizedInvestmentGainLossMember_label_en-US" xlink:label="lab_us-gaap_AccumulatedNetUnrealizedInvestmentGainLossMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">AOCI, Accumulated Gain (Loss), Debt Securities, Available-for-Sale, Parent [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AccumulatedNetUnrealizedInvestmentGainLossMember" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_AccumulatedNetUnrealizedInvestmentGainLossMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AccumulatedNetUnrealizedInvestmentGainLossMember" xlink:to="lab_us-gaap_AccumulatedNetUnrealizedInvestmentGainLossMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_PreferredStockSharesIssued_f3a62dc9-cfea-462f-b798-4347753a1970_terseLabel_en-US" xlink:label="lab_us-gaap_PreferredStockSharesIssued" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Preferred stock, shares issued (in shares)</link:label>
    <link:label id="lab_us-gaap_PreferredStockSharesIssued_label_en-US" xlink:label="lab_us-gaap_PreferredStockSharesIssued" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Preferred Stock, Shares Issued</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PreferredStockSharesIssued" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_PreferredStockSharesIssued"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PreferredStockSharesIssued" xlink:to="lab_us-gaap_PreferredStockSharesIssued" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_DocumentType_c1f9281d-ddc6-4545-a969-041c864e7977_terseLabel_en-US" xlink:label="lab_dei_DocumentType" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Document Type</link:label>
    <link:label id="lab_dei_DocumentType_label_en-US" xlink:label="lab_dei_DocumentType" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Document Type</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_DocumentType" xlink:href="https://xbrl.sec.gov/dei/2022/dei-2022.xsd#dei_DocumentType"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_DocumentType" xlink:to="lab_dei_DocumentType" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardOptionsOutstandingWeightedAverageExercisePriceRollforward_81c3968d-3cf1-4b38-83bf-a1a3602f3eef_terseLabel_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardOptionsOutstandingWeightedAverageExercisePriceRollforward" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Weighted-Average Exercise Price</link:label>
    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardOptionsOutstandingWeightedAverageExercisePriceRollforward_label_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardOptionsOutstandingWeightedAverageExercisePriceRollforward" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Share-Based Compensation Arrangement by Share-Based Payment Award, Options, Outstanding, Weighted Average Exercise Price [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardOptionsOutstandingWeightedAverageExercisePriceRollforward" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardOptionsOutstandingWeightedAverageExercisePriceRollforward"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardOptionsOutstandingWeightedAverageExercisePriceRollforward" xlink:to="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardOptionsOutstandingWeightedAverageExercisePriceRollforward" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_SecuredOvernightFinancingRateSofrOvernightIndexSwapRateMember_f7481d61-3b11-48d8-95fa-bad380665598_terseLabel_en-US" xlink:label="lab_us-gaap_SecuredOvernightFinancingRateSofrOvernightIndexSwapRateMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">SOFR</link:label>
    <link:label id="lab_us-gaap_SecuredOvernightFinancingRateSofrOvernightIndexSwapRateMember_label_en-US" xlink:label="lab_us-gaap_SecuredOvernightFinancingRateSofrOvernightIndexSwapRateMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Secured Overnight Financing Rate (SOFR) Overnight Index Swap Rate [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SecuredOvernightFinancingRateSofrOvernightIndexSwapRateMember" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_SecuredOvernightFinancingRateSofrOvernightIndexSwapRateMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_SecuredOvernightFinancingRateSofrOvernightIndexSwapRateMember" xlink:to="lab_us-gaap_SecuredOvernightFinancingRateSofrOvernightIndexSwapRateMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleRealizedGainLoss_260f739b-f1c5-46e2-91db-d1471b1f7dbc_totalLabel_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleRealizedGainLoss" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Net realized gains on investments</link:label>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleRealizedGainLoss_label_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleRealizedGainLoss" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt Securities, Available-for-Sale, Realized Gain (Loss)</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtSecuritiesAvailableForSaleRealizedGainLoss" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_DebtSecuritiesAvailableForSaleRealizedGainLoss"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DebtSecuritiesAvailableForSaleRealizedGainLoss" xlink:to="lab_us-gaap_DebtSecuritiesAvailableForSaleRealizedGainLoss" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedRollForward_1de85205-5717-45d6-8f62-c849e8d28350_terseLabel_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedRollForward" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Number of Shares</link:label>
    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedRollForward_label_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedRollForward" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Share-Based Compensation Arrangement by Share-Based Payment Award, Equity Instruments Other than Options, Nonvested, Number of Shares [Roll Forward]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedRollForward" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedRollForward"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedRollForward" xlink:to="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedRollForward" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ConcentrationRiskBenchmarkDomain_64e11c84-06b2-48f3-bcdc-967a8b0dae7a_terseLabel_en-US" xlink:label="lab_us-gaap_ConcentrationRiskBenchmarkDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Concentration Risk Benchmark [Domain]</link:label>
    <link:label id="lab_us-gaap_ConcentrationRiskBenchmarkDomain_label_en-US" xlink:label="lab_us-gaap_ConcentrationRiskBenchmarkDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Concentration Risk Benchmark [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ConcentrationRiskBenchmarkDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ConcentrationRiskBenchmarkDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ConcentrationRiskBenchmarkDomain" xlink:to="lab_us-gaap_ConcentrationRiskBenchmarkDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardOptionsForfeituresAndExpirationsInPeriod_ccedabe8-6697-497d-bb17-db61c1ef8e77_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardOptionsForfeituresAndExpirationsInPeriod" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Forfeited, expired or canceled (in shares)</link:label>
    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardOptionsForfeituresAndExpirationsInPeriod_label_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardOptionsForfeituresAndExpirationsInPeriod" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Share-Based Compensation Arrangement by Share-Based Payment Award, Options, Forfeitures and Expirations in Period</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardOptionsForfeituresAndExpirationsInPeriod" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardOptionsForfeituresAndExpirationsInPeriod"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardOptionsForfeituresAndExpirationsInPeriod" xlink:to="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardOptionsForfeituresAndExpirationsInPeriod" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AssetsFairValueDisclosureAbstract_a020fb17-9835-4ebe-bf20-5517e49691f3_terseLabel_en-US" xlink:label="lab_us-gaap_AssetsFairValueDisclosureAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Assets</link:label>
    <link:label id="lab_us-gaap_AssetsFairValueDisclosureAbstract_label_en-US" xlink:label="lab_us-gaap_AssetsFairValueDisclosureAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Assets, Fair Value Disclosure [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AssetsFairValueDisclosureAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_AssetsFairValueDisclosureAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AssetsFairValueDisclosureAbstract" xlink:to="lab_us-gaap_AssetsFairValueDisclosureAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_RestructuringCostAndReserveAxis_563d43b2-c38d-42d4-852a-9c1c310decb9_terseLabel_en-US" xlink:label="lab_us-gaap_RestructuringCostAndReserveAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Restructuring Type [Axis]</link:label>
    <link:label id="lab_us-gaap_RestructuringCostAndReserveAxis_label_en-US" xlink:label="lab_us-gaap_RestructuringCostAndReserveAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Restructuring Type [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_RestructuringCostAndReserveAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_RestructuringCostAndReserveAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_RestructuringCostAndReserveAxis" xlink:to="lab_us-gaap_RestructuringCostAndReserveAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedWeightedAverageGrantDateFairValue_85091486-67ac-413a-b2ab-ec651c81e691_periodStartLabel_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedWeightedAverageGrantDateFairValue" xlink:role="http://www.xbrl.org/2003/role/periodStartLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Beginning balance, weighted-average grant date fair value (in dollars per share)</link:label>
    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedWeightedAverageGrantDateFairValue_5a1747a8-98f0-43c7-a295-09faf0481f49_periodEndLabel_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedWeightedAverageGrantDateFairValue" xlink:role="http://www.xbrl.org/2003/role/periodEndLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Ending balance, weighted-average grant date fair value (in dollars per share)</link:label>
    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedWeightedAverageGrantDateFairValue_label_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedWeightedAverageGrantDateFairValue" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Share-Based Compensation Arrangement by Share-Based Payment Award, Equity Instruments Other than Options, Nonvested, Weighted Average Grant Date Fair Value</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedWeightedAverageGrantDateFairValue" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedWeightedAverageGrantDateFairValue"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedWeightedAverageGrantDateFairValue" xlink:to="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedWeightedAverageGrantDateFairValue" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DebtDisclosureTextBlock_8a1e05cb-b497-413a-9381-d4c2ceaafac2_terseLabel_en-US" xlink:label="lab_us-gaap_DebtDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">LONG-TERM DEBT</link:label>
    <link:label id="lab_us-gaap_DebtDisclosureTextBlock_label_en-US" xlink:label="lab_us-gaap_DebtDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt Disclosure [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtDisclosureTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_DebtDisclosureTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DebtDisclosureTextBlock" xlink:to="lab_us-gaap_DebtDisclosureTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_EntityShellCompany_578c5e84-3de2-45f5-8e14-f97130423579_terseLabel_en-US" xlink:label="lab_dei_EntityShellCompany" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Entity Shell Company</link:label>
    <link:label id="lab_dei_EntityShellCompany_label_en-US" xlink:label="lab_dei_EntityShellCompany" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Entity Shell Company</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_EntityShellCompany" xlink:href="https://xbrl.sec.gov/dei/2022/dei-2022.xsd#dei_EntityShellCompany"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_EntityShellCompany" xlink:to="lab_dei_EntityShellCompany" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CommonClassBMember_4b25e2d7-a717-446e-818e-ae205fa32ff2_terseLabel_en-US" xlink:label="lab_us-gaap_CommonClassBMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Class B Shares</link:label>
    <link:label id="lab_us-gaap_CommonClassBMember_label_en-US" xlink:label="lab_us-gaap_CommonClassBMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Common Class B [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CommonClassBMember" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_CommonClassBMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CommonClassBMember" xlink:to="lab_us-gaap_CommonClassBMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_InvestmentsAbstract_977734d1-e79c-47f2-adce-aa5db18ba808_terseLabel_en-US" xlink:label="lab_us-gaap_InvestmentsAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Investments:</link:label>
    <link:label id="lab_us-gaap_InvestmentsAbstract_label_en-US" xlink:label="lab_us-gaap_InvestmentsAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Investments [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_InvestmentsAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_InvestmentsAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_InvestmentsAbstract" xlink:to="lab_us-gaap_InvestmentsAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DirectPremiumsEarned_23b060a6-0cb2-4aa0-b164-ada3b536f9cd_terseLabel_en-US" xlink:label="lab_us-gaap_DirectPremiumsEarned" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Direct</link:label>
    <link:label id="lab_us-gaap_DirectPremiumsEarned_label_en-US" xlink:label="lab_us-gaap_DirectPremiumsEarned" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Direct Premiums Earned</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DirectPremiumsEarned" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_DirectPremiumsEarned"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DirectPremiumsEarned" xlink:to="lab_us-gaap_DirectPremiumsEarned" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_InvestmentIncomeTextBlock_6f5b13d8-ca32-4636-9bd4-ac19cdf94352_terseLabel_en-US" xlink:label="lab_us-gaap_InvestmentIncomeTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Schedule of Net Investment Income</link:label>
    <link:label id="lab_us-gaap_InvestmentIncomeTextBlock_label_en-US" xlink:label="lab_us-gaap_InvestmentIncomeTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Investment Income [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_InvestmentIncomeTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_InvestmentIncomeTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_InvestmentIncomeTextBlock" xlink:to="lab_us-gaap_InvestmentIncomeTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_root_DebtInstrumentCovenantComplianceDomain_5e1ba55f-7874-4c1c-a021-bf1168826d2a_terseLabel_en-US" xlink:label="lab_root_DebtInstrumentCovenantComplianceDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt Instrument, Covenant Compliance [Domain]</link:label>
    <link:label id="lab_root_DebtInstrumentCovenantComplianceDomain_label_en-US" xlink:label="lab_root_DebtInstrumentCovenantComplianceDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt Instrument, Covenant Compliance [Domain]</link:label>
    <link:label id="lab_root_DebtInstrumentCovenantComplianceDomain_documentation_en-US" xlink:label="lab_root_DebtInstrumentCovenantComplianceDomain" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt Instrument, Covenant Compliance [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_root_DebtInstrumentCovenantComplianceDomain" xlink:href="root-20220930.xsd#root_DebtInstrumentCovenantComplianceDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_root_DebtInstrumentCovenantComplianceDomain" xlink:to="lab_root_DebtInstrumentCovenantComplianceDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ScheduleOfInvestmentIncomeReportedAmountsByCategoryLineItems_e5a4aba2-3d5e-4e43-8795-5afc81e4ed01_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfInvestmentIncomeReportedAmountsByCategoryLineItems" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Net Investment Income [Line Items]</link:label>
    <link:label id="lab_us-gaap_ScheduleOfInvestmentIncomeReportedAmountsByCategoryLineItems_label_en-US" xlink:label="lab_us-gaap_ScheduleOfInvestmentIncomeReportedAmountsByCategoryLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Net Investment Income [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfInvestmentIncomeReportedAmountsByCategoryLineItems" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ScheduleOfInvestmentIncomeReportedAmountsByCategoryLineItems"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ScheduleOfInvestmentIncomeReportedAmountsByCategoryLineItems" xlink:to="lab_us-gaap_ScheduleOfInvestmentIncomeReportedAmountsByCategoryLineItems" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FinancialInstrumentAxis_5ef79455-21d5-40c9-8ddf-433f366e5ea4_terseLabel_en-US" xlink:label="lab_us-gaap_FinancialInstrumentAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Financial Instrument [Axis]</link:label>
    <link:label id="lab_us-gaap_FinancialInstrumentAxis_label_en-US" xlink:label="lab_us-gaap_FinancialInstrumentAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Financial Instrument [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FinancialInstrumentAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_FinancialInstrumentAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FinancialInstrumentAxis" xlink:to="lab_us-gaap_FinancialInstrumentAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_OtherInvestments_e2c216b5-5be1-4afe-8031-1570c8d86f5f_terseLabel_en-US" xlink:label="lab_us-gaap_OtherInvestments" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Other investments</link:label>
    <link:label id="lab_us-gaap_OtherInvestments_label_en-US" xlink:label="lab_us-gaap_OtherInvestments" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Other Investments</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OtherInvestments" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_OtherInvestments"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_OtherInvestments" xlink:to="lab_us-gaap_OtherInvestments" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_SubsequentEventMember_d692ff35-c9f1-44d9-afeb-d6121df1949e_terseLabel_en-US" xlink:label="lab_us-gaap_SubsequentEventMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Subsequent event</link:label>
    <link:label id="lab_us-gaap_SubsequentEventMember_label_en-US" xlink:label="lab_us-gaap_SubsequentEventMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Subsequent Event [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SubsequentEventMember" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_SubsequentEventMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_SubsequentEventMember" xlink:to="lab_us-gaap_SubsequentEventMember" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_DocumentPeriodEndDate_e781d092-ef70-420e-b09b-7e14b4c4b59f_terseLabel_en-US" xlink:label="lab_dei_DocumentPeriodEndDate" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Document Period End Date</link:label>
    <link:label id="lab_dei_DocumentPeriodEndDate_label_en-US" xlink:label="lab_dei_DocumentPeriodEndDate" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Document Period End Date</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_DocumentPeriodEndDate" xlink:href="https://xbrl.sec.gov/dei/2022/dei-2022.xsd#dei_DocumentPeriodEndDate"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_DocumentPeriodEndDate" xlink:to="lab_dei_DocumentPeriodEndDate" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ShareBasedCompensationAwardTrancheOneMember_8dbbfb1b-64b4-4fce-9a95-bd52b9bbed4f_terseLabel_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationAwardTrancheOneMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Tranche 1</link:label>
    <link:label id="lab_us-gaap_ShareBasedCompensationAwardTrancheOneMember_label_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationAwardTrancheOneMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Share-Based Payment Arrangement, Tranche One [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShareBasedCompensationAwardTrancheOneMember" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ShareBasedCompensationAwardTrancheOneMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ShareBasedCompensationAwardTrancheOneMember" xlink:to="lab_us-gaap_ShareBasedCompensationAwardTrancheOneMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AdjustmentsToAdditionalPaidInCapitalStockIssuedIssuanceCosts_f0a90523-e621-4d96-8bea-5e3180cb94a6_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_AdjustmentsToAdditionalPaidInCapitalStockIssuedIssuanceCosts" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Warrants issuance costs</link:label>
    <link:label id="lab_us-gaap_AdjustmentsToAdditionalPaidInCapitalStockIssuedIssuanceCosts_label_en-US" xlink:label="lab_us-gaap_AdjustmentsToAdditionalPaidInCapitalStockIssuedIssuanceCosts" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Adjustments to Additional Paid in Capital, Stock Issued, Issuance Costs</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AdjustmentsToAdditionalPaidInCapitalStockIssuedIssuanceCosts" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_AdjustmentsToAdditionalPaidInCapitalStockIssuedIssuanceCosts"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AdjustmentsToAdditionalPaidInCapitalStockIssuedIssuanceCosts" xlink:to="lab_us-gaap_AdjustmentsToAdditionalPaidInCapitalStockIssuedIssuanceCosts" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FairValueLiabilitiesMeasuredOnRecurringAndNonrecurringBasisTableTextBlock_eef5a50b-c8a0-4e6c-a4fa-9f97ab7163d9_terseLabel_en-US" xlink:label="lab_us-gaap_FairValueLiabilitiesMeasuredOnRecurringAndNonrecurringBasisTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Schedule of Carrying Amounts and Fair Values of Financial Instruments</link:label>
    <link:label id="lab_us-gaap_FairValueLiabilitiesMeasuredOnRecurringAndNonrecurringBasisTableTextBlock_label_en-US" xlink:label="lab_us-gaap_FairValueLiabilitiesMeasuredOnRecurringAndNonrecurringBasisTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Fair Value, Liabilities Measured on Recurring and Nonrecurring Basis [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueLiabilitiesMeasuredOnRecurringAndNonrecurringBasisTableTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_FairValueLiabilitiesMeasuredOnRecurringAndNonrecurringBasisTableTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FairValueLiabilitiesMeasuredOnRecurringAndNonrecurringBasisTableTextBlock" xlink:to="lab_us-gaap_FairValueLiabilitiesMeasuredOnRecurringAndNonrecurringBasisTableTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_root_StandardPoorsAAPlusAAAAMinusAMinusOneRatingMember_7f4da9e3-3988-4a2d-b206-7fa51a523007_terseLabel_en-US" xlink:label="lab_root_StandardPoorsAAPlusAAAAMinusAMinusOneRatingMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">AA+, AA, AA-, A-1</link:label>
    <link:label id="lab_root_StandardPoorsAAPlusAAAAMinusAMinusOneRatingMember_label_en-US" xlink:label="lab_root_StandardPoorsAAPlusAAAAMinusAMinusOneRatingMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Standard &amp; Poor's, AA Plus, AA, AA Minus, A Minus One Rating [Member]</link:label>
    <link:label id="lab_root_StandardPoorsAAPlusAAAAMinusAMinusOneRatingMember_documentation_en-US" xlink:label="lab_root_StandardPoorsAAPlusAAAAMinusAMinusOneRatingMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Standard &amp; Poor's, AA Plus, AA, AA Minus, A Minus One Rating</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_root_StandardPoorsAAPlusAAAAMinusAMinusOneRatingMember" xlink:href="root-20220930.xsd#root_StandardPoorsAAPlusAAAAMinusAMinusOneRatingMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_root_StandardPoorsAAPlusAAAAMinusAMinusOneRatingMember" xlink:to="lab_root_StandardPoorsAAPlusAAAAMinusAMinusOneRatingMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleTable_934d09d2-3f7c-40f4-8a88-2a7a5d429619_terseLabel_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt Securities, Available-for-sale [Table]</link:label>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleTable_label_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleTable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt Securities, Available-for-Sale [Table]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtSecuritiesAvailableForSaleTable" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_DebtSecuritiesAvailableForSaleTable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DebtSecuritiesAvailableForSaleTable" xlink:to="lab_us-gaap_DebtSecuritiesAvailableForSaleTable" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ScheduleOfAccumulatedOtherComprehensiveIncomeLossTableTextBlock_c766fa81-76ac-4aa2-bf76-9f589a654c22_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfAccumulatedOtherComprehensiveIncomeLossTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Schedule of AOCI</link:label>
    <link:label id="lab_us-gaap_ScheduleOfAccumulatedOtherComprehensiveIncomeLossTableTextBlock_label_en-US" xlink:label="lab_us-gaap_ScheduleOfAccumulatedOtherComprehensiveIncomeLossTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Schedule of Accumulated Other Comprehensive Income (Loss) [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfAccumulatedOtherComprehensiveIncomeLossTableTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ScheduleOfAccumulatedOtherComprehensiveIncomeLossTableTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ScheduleOfAccumulatedOtherComprehensiveIncomeLossTableTextBlock" xlink:to="lab_us-gaap_ScheduleOfAccumulatedOtherComprehensiveIncomeLossTableTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_Assets_3f6b3a5c-c93e-4999-98e7-4c91b4158687_totalLabel_en-US" xlink:label="lab_us-gaap_Assets" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Total assets</link:label>
    <link:label id="lab_us-gaap_Assets_label_en-US" xlink:label="lab_us-gaap_Assets" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Assets</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_Assets" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_Assets"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_Assets" xlink:to="lab_us-gaap_Assets" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_PaymentsForLossesAndLossAdjustmentExpense_e41fe638-df74-48dd-949b-4f1e32d63564_totalLabel_en-US" xlink:label="lab_us-gaap_PaymentsForLossesAndLossAdjustmentExpense" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Total paid</link:label>
    <link:label id="lab_us-gaap_PaymentsForLossesAndLossAdjustmentExpense_label_en-US" xlink:label="lab_us-gaap_PaymentsForLossesAndLossAdjustmentExpense" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Liability for Unpaid Claims and Claims Adjustment Expense, Claims Paid</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PaymentsForLossesAndLossAdjustmentExpense" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_PaymentsForLossesAndLossAdjustmentExpense"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PaymentsForLossesAndLossAdjustmentExpense" xlink:to="lab_us-gaap_PaymentsForLossesAndLossAdjustmentExpense" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DebtDisclosureAbstract_label_en-US" xlink:label="lab_us-gaap_DebtDisclosureAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt Disclosure [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtDisclosureAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_DebtDisclosureAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DebtDisclosureAbstract" xlink:to="lab_us-gaap_DebtDisclosureAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EarningsPerShareAbstract_label_en-US" xlink:label="lab_us-gaap_EarningsPerShareAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Earnings Per Share [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EarningsPerShareAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_EarningsPerShareAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EarningsPerShareAbstract" xlink:to="lab_us-gaap_EarningsPerShareAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_IncomeStatementLocationAxis_8f33c988-9b96-4d50-98c4-4a54297c1dfa_terseLabel_en-US" xlink:label="lab_us-gaap_IncomeStatementLocationAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Income Statement Location [Axis]</link:label>
    <link:label id="lab_us-gaap_IncomeStatementLocationAxis_label_en-US" xlink:label="lab_us-gaap_IncomeStatementLocationAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Income Statement Location [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncomeStatementLocationAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_IncomeStatementLocationAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IncomeStatementLocationAxis" xlink:to="lab_us-gaap_IncomeStatementLocationAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ShareBasedCompensationAwardTrancheThreeMember_c88f56ea-aa53-4a6a-9c86-e298e595cf83_terseLabel_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationAwardTrancheThreeMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Tranche 3</link:label>
    <link:label id="lab_us-gaap_ShareBasedCompensationAwardTrancheThreeMember_label_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationAwardTrancheThreeMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Share-Based Payment Arrangement, Tranche Three [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShareBasedCompensationAwardTrancheThreeMember" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ShareBasedCompensationAwardTrancheThreeMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ShareBasedCompensationAwardTrancheThreeMember" xlink:to="lab_us-gaap_ShareBasedCompensationAwardTrancheThreeMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareByAntidilutiveSecuritiesAxis_8a694155-5bef-4c2c-aaff-bc6cbe6bd381_terseLabel_en-US" xlink:label="lab_us-gaap_AntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareByAntidilutiveSecuritiesAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Antidilutive Securities [Axis]</link:label>
    <link:label id="lab_us-gaap_AntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareByAntidilutiveSecuritiesAxis_label_en-US" xlink:label="lab_us-gaap_AntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareByAntidilutiveSecuritiesAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Antidilutive Securities [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareByAntidilutiveSecuritiesAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_AntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareByAntidilutiveSecuritiesAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareByAntidilutiveSecuritiesAxis" xlink:to="lab_us-gaap_AntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareByAntidilutiveSecuritiesAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FairValueConcentrationOfRiskTextBlock_5da53530-6602-4a0b-bee0-f07e5cd79390_terseLabel_en-US" xlink:label="lab_us-gaap_FairValueConcentrationOfRiskTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Schedule of Credit Ratings</link:label>
    <link:label id="lab_us-gaap_FairValueConcentrationOfRiskTextBlock_label_en-US" xlink:label="lab_us-gaap_FairValueConcentrationOfRiskTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Fair Value, Concentration of Risk [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueConcentrationOfRiskTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_FairValueConcentrationOfRiskTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FairValueConcentrationOfRiskTextBlock" xlink:to="lab_us-gaap_FairValueConcentrationOfRiskTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ScheduleOfRestructuringAndRelatedCostsTable_f40c7aa5-9c90-467a-aa2e-ddeff1047e48_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfRestructuringAndRelatedCostsTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Schedule of Restructuring and Related Costs [Table]</link:label>
    <link:label id="lab_us-gaap_ScheduleOfRestructuringAndRelatedCostsTable_label_en-US" xlink:label="lab_us-gaap_ScheduleOfRestructuringAndRelatedCostsTable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Schedule of Restructuring and Related Costs [Table]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfRestructuringAndRelatedCostsTable" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ScheduleOfRestructuringAndRelatedCostsTable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ScheduleOfRestructuringAndRelatedCostsTable" xlink:to="lab_us-gaap_ScheduleOfRestructuringAndRelatedCostsTable" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementsByShareBasedPaymentAwardOptionsExercisesInPeriodWeightedAverageExercisePrice_2e2dc9e9-b872-4d03-a321-13716f696641_terseLabel_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementsByShareBasedPaymentAwardOptionsExercisesInPeriodWeightedAverageExercisePrice" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Exercised, weighted-average exercise price (in dollars per share)</link:label>
    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementsByShareBasedPaymentAwardOptionsExercisesInPeriodWeightedAverageExercisePrice_label_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementsByShareBasedPaymentAwardOptionsExercisesInPeriodWeightedAverageExercisePrice" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Share-Based Compensation Arrangements by Share-Based Payment Award, Options, Exercises in Period, Weighted Average Exercise Price</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShareBasedCompensationArrangementsByShareBasedPaymentAwardOptionsExercisesInPeriodWeightedAverageExercisePrice" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ShareBasedCompensationArrangementsByShareBasedPaymentAwardOptionsExercisesInPeriodWeightedAverageExercisePrice"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ShareBasedCompensationArrangementsByShareBasedPaymentAwardOptionsExercisesInPeriodWeightedAverageExercisePrice" xlink:to="lab_us-gaap_ShareBasedCompensationArrangementsByShareBasedPaymentAwardOptionsExercisesInPeriodWeightedAverageExercisePrice" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_NetCashProvidedByUsedInFinancingActivities_8b5c6a41-a789-4530-a27d-d28bd6effd95_totalLabel_en-US" xlink:label="lab_us-gaap_NetCashProvidedByUsedInFinancingActivities" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Net cash provided by financing activities</link:label>
    <link:label id="lab_us-gaap_NetCashProvidedByUsedInFinancingActivities_label_en-US" xlink:label="lab_us-gaap_NetCashProvidedByUsedInFinancingActivities" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Net Cash Provided by (Used in) Financing Activities</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NetCashProvidedByUsedInFinancingActivities" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_NetCashProvidedByUsedInFinancingActivities"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_NetCashProvidedByUsedInFinancingActivities" xlink:to="lab_us-gaap_NetCashProvidedByUsedInFinancingActivities" xlink:type="arc" order="1"/>
    <link:label id="lab_root_PaymentsForAssetAcquisitions_b0a8cf27-2a71-4c75-be79-5991de7ec07d_negatedTerseLabel_en-US" xlink:label="lab_root_PaymentsForAssetAcquisitions" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Purchases of indefinite-lived intangible assets and transaction costs</link:label>
    <link:label id="lab_root_PaymentsForAssetAcquisitions_label_en-US" xlink:label="lab_root_PaymentsForAssetAcquisitions" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Payments For Asset Acquisitions</link:label>
    <link:label id="lab_root_PaymentsForAssetAcquisitions_documentation_en-US" xlink:label="lab_root_PaymentsForAssetAcquisitions" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Payments For Asset Acquisitions</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_root_PaymentsForAssetAcquisitions" xlink:href="root-20220930.xsd#root_PaymentsForAssetAcquisitions"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_root_PaymentsForAssetAcquisitions" xlink:to="lab_root_PaymentsForAssetAcquisitions" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LongTermDebtFairValue_3a893a4a-d786-4132-a3e2-0beb33262d4b_terseLabel_en-US" xlink:label="lab_us-gaap_LongTermDebtFairValue" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Long-term debt</link:label>
    <link:label id="lab_us-gaap_LongTermDebtFairValue_label_en-US" xlink:label="lab_us-gaap_LongTermDebtFairValue" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Long-Term Debt, Fair Value</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LongTermDebtFairValue" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_LongTermDebtFairValue"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LongTermDebtFairValue" xlink:to="lab_us-gaap_LongTermDebtFairValue" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AccountingPoliciesAbstract_db5916d5-076e-46ae-94de-8ca28839952f_terseLabel_en-US" xlink:label="lab_us-gaap_AccountingPoliciesAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Accounting Policies [Abstract]</link:label>
    <link:label id="lab_us-gaap_AccountingPoliciesAbstract_label_en-US" xlink:label="lab_us-gaap_AccountingPoliciesAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Accounting Policies [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AccountingPoliciesAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_AccountingPoliciesAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AccountingPoliciesAbstract" xlink:to="lab_us-gaap_AccountingPoliciesAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ReclassificationFromAociCurrentPeriodNetOfTaxAttributableToParent_b25e9221-b40e-492f-b6a5-01f3437ddf8c_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_ReclassificationFromAociCurrentPeriodNetOfTaxAttributableToParent" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Net realized losses (gains) on investments reclassified from AOCI to net loss</link:label>
    <link:label id="lab_us-gaap_ReclassificationFromAociCurrentPeriodNetOfTaxAttributableToParent_label_en-US" xlink:label="lab_us-gaap_ReclassificationFromAociCurrentPeriodNetOfTaxAttributableToParent" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Reclassification from AOCI, Current Period, Net of Tax, Attributable to Parent</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ReclassificationFromAociCurrentPeriodNetOfTaxAttributableToParent" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ReclassificationFromAociCurrentPeriodNetOfTaxAttributableToParent"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ReclassificationFromAociCurrentPeriodNetOfTaxAttributableToParent" xlink:to="lab_us-gaap_ReclassificationFromAociCurrentPeriodNetOfTaxAttributableToParent" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_PremiumsWrittenGross_52636d2c-f7c8-4fd0-a574-87a5279b3d09_terseLabel_en-US" xlink:label="lab_us-gaap_PremiumsWrittenGross" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Total</link:label>
    <link:label id="lab_us-gaap_PremiumsWrittenGross_label_en-US" xlink:label="lab_us-gaap_PremiumsWrittenGross" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Premiums Written, Gross</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PremiumsWrittenGross" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_PremiumsWrittenGross"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PremiumsWrittenGross" xlink:to="lab_us-gaap_PremiumsWrittenGross" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_TemporaryEquityCarryingAmountAttributableToParent_67c04da0-c874-4f33-be07-6685e7ee3c43_terseLabel_en-US" xlink:label="lab_us-gaap_TemporaryEquityCarryingAmountAttributableToParent" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Redeemable convertible preferred stock, $0.0001 par value, 100.0 shares authorized, 14.1 shares issued and outstanding at September&#160;30, 2022 and December&#160;31, 2021 (liquidation preference of $126.5)</link:label>
    <link:label id="lab_us-gaap_TemporaryEquityCarryingAmountAttributableToParent_6dcb2fdd-d5e8-4f62-8ead-cfbd5ed02c96_periodStartLabel_en-US" xlink:label="lab_us-gaap_TemporaryEquityCarryingAmountAttributableToParent" xlink:role="http://www.xbrl.org/2003/role/periodStartLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Beginning balance</link:label>
    <link:label id="lab_us-gaap_TemporaryEquityCarryingAmountAttributableToParent_02ccc577-9e09-40ca-9946-542ef33aabb5_periodEndLabel_en-US" xlink:label="lab_us-gaap_TemporaryEquityCarryingAmountAttributableToParent" xlink:role="http://www.xbrl.org/2003/role/periodEndLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Ending balance</link:label>
    <link:label id="lab_us-gaap_TemporaryEquityCarryingAmountAttributableToParent_label_en-US" xlink:label="lab_us-gaap_TemporaryEquityCarryingAmountAttributableToParent" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Temporary Equity, Carrying Amount, Attributable to Parent</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_TemporaryEquityCarryingAmountAttributableToParent" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_TemporaryEquityCarryingAmountAttributableToParent"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_TemporaryEquityCarryingAmountAttributableToParent" xlink:to="lab_us-gaap_TemporaryEquityCarryingAmountAttributableToParent" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_IncomeLossFromContinuingOperationsBeforeIncomeTaxesExtraordinaryItemsNoncontrollingInterest_bf989b9d-b2eb-436c-b9f8-aadcc5ac93bc_totalLabel_en-US" xlink:label="lab_us-gaap_IncomeLossFromContinuingOperationsBeforeIncomeTaxesExtraordinaryItemsNoncontrollingInterest" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Loss before income tax expense</link:label>
    <link:label id="lab_us-gaap_IncomeLossFromContinuingOperationsBeforeIncomeTaxesExtraordinaryItemsNoncontrollingInterest_label_en-US" xlink:label="lab_us-gaap_IncomeLossFromContinuingOperationsBeforeIncomeTaxesExtraordinaryItemsNoncontrollingInterest" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Income (Loss) from Continuing Operations before Income Taxes, Noncontrolling Interest</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncomeLossFromContinuingOperationsBeforeIncomeTaxesExtraordinaryItemsNoncontrollingInterest" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_IncomeLossFromContinuingOperationsBeforeIncomeTaxesExtraordinaryItemsNoncontrollingInterest"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IncomeLossFromContinuingOperationsBeforeIncomeTaxesExtraordinaryItemsNoncontrollingInterest" xlink:to="lab_us-gaap_IncomeLossFromContinuingOperationsBeforeIncomeTaxesExtraordinaryItemsNoncontrollingInterest" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_StockholdersEquityAbstract_d0c43305-63cf-447f-89f5-d2d0b5b0ae6f_terseLabel_en-US" xlink:label="lab_us-gaap_StockholdersEquityAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Stockholders&#8217; equity:</link:label>
    <link:label id="lab_us-gaap_StockholdersEquityAbstract_label_en-US" xlink:label="lab_us-gaap_StockholdersEquityAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Stockholders' Equity Attributable to Parent [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_StockholdersEquityAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_StockholdersEquityAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_StockholdersEquityAbstract" xlink:to="lab_us-gaap_StockholdersEquityAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EarningsPerShareTextBlock_76fc5b34-514b-48ed-aee7-cc40e9e7ea8f_terseLabel_en-US" xlink:label="lab_us-gaap_EarningsPerShareTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">LOSS PER SHARE</link:label>
    <link:label id="lab_us-gaap_EarningsPerShareTextBlock_label_en-US" xlink:label="lab_us-gaap_EarningsPerShareTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Earnings Per Share [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EarningsPerShareTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_EarningsPerShareTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EarningsPerShareTextBlock" xlink:to="lab_us-gaap_EarningsPerShareTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterOneThroughFiveYearsAmortizedCost_3403dec9-c214-496a-b480-813b05631713_terseLabel_en-US" xlink:label="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterOneThroughFiveYearsAmortizedCost" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Due after one year through five years</link:label>
    <link:label id="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterOneThroughFiveYearsAmortizedCost_label_en-US" xlink:label="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterOneThroughFiveYearsAmortizedCost" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt Securities, Available-for-Sale, Amortized Cost, Maturity, Allocated and Single Maturity Date, after Year One Through Five</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterOneThroughFiveYearsAmortizedCost" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterOneThroughFiveYearsAmortizedCost"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterOneThroughFiveYearsAmortizedCost" xlink:to="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterOneThroughFiveYearsAmortizedCost" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ReinsuranceRecoverableForUnpaidClaimsAndClaimsAdjustments_0a06ee9f-8cf7-4ec9-a6db-cac275256c34_negatedPeriodStartLabel_en-US" xlink:label="lab_us-gaap_ReinsuranceRecoverableForUnpaidClaimsAndClaimsAdjustments" xlink:role="http://www.xbrl.org/2009/role/negatedPeriodStartLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Reinsurance recoverable on unpaid losses</link:label>
    <link:label id="lab_us-gaap_ReinsuranceRecoverableForUnpaidClaimsAndClaimsAdjustments_a130f7d2-346a-43e2-a1d0-8a206c61c696_periodEndLabel_en-US" xlink:label="lab_us-gaap_ReinsuranceRecoverableForUnpaidClaimsAndClaimsAdjustments" xlink:role="http://www.xbrl.org/2003/role/periodEndLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Plus reinsurance recoverable on unpaid losses</link:label>
    <link:label id="lab_us-gaap_ReinsuranceRecoverableForUnpaidClaimsAndClaimsAdjustments_label_en-US" xlink:label="lab_us-gaap_ReinsuranceRecoverableForUnpaidClaimsAndClaimsAdjustments" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Reinsurance Recoverable for Unpaid Claims and Claims Adjustments</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ReinsuranceRecoverableForUnpaidClaimsAndClaimsAdjustments" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ReinsuranceRecoverableForUnpaidClaimsAndClaimsAdjustments"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ReinsuranceRecoverableForUnpaidClaimsAndClaimsAdjustments" xlink:to="lab_us-gaap_ReinsuranceRecoverableForUnpaidClaimsAndClaimsAdjustments" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_MunicipalBondsMember_6361eb0b-32d8-418c-9344-7c84eba2fed9_terseLabel_en-US" xlink:label="lab_us-gaap_MunicipalBondsMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Municipal securities</link:label>
    <link:label id="lab_us-gaap_MunicipalBondsMember_label_en-US" xlink:label="lab_us-gaap_MunicipalBondsMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Municipal Bonds [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_MunicipalBondsMember" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_MunicipalBondsMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_MunicipalBondsMember" xlink:to="lab_us-gaap_MunicipalBondsMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ShortTermInvestmentsMember_6cb5ab8c-8d99-4c7d-b5e0-e0f742f7de72_terseLabel_en-US" xlink:label="lab_us-gaap_ShortTermInvestmentsMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Short-term investments</link:label>
    <link:label id="lab_us-gaap_ShortTermInvestmentsMember_label_en-US" xlink:label="lab_us-gaap_ShortTermInvestmentsMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Short-Term Investments [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShortTermInvestmentsMember" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ShortTermInvestmentsMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ShortTermInvestmentsMember" xlink:to="lab_us-gaap_ShortTermInvestmentsMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementsByShareBasedPaymentAwardAwardTypeAndPlanNameDomain_70b778b0-25b1-4790-8829-634f5877d482_terseLabel_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementsByShareBasedPaymentAwardAwardTypeAndPlanNameDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Award Type [Domain]</link:label>
    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementsByShareBasedPaymentAwardAwardTypeAndPlanNameDomain_label_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementsByShareBasedPaymentAwardAwardTypeAndPlanNameDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Award Type [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShareBasedCompensationArrangementsByShareBasedPaymentAwardAwardTypeAndPlanNameDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ShareBasedCompensationArrangementsByShareBasedPaymentAwardAwardTypeAndPlanNameDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ShareBasedCompensationArrangementsByShareBasedPaymentAwardAwardTypeAndPlanNameDomain" xlink:to="lab_us-gaap_ShareBasedCompensationArrangementsByShareBasedPaymentAwardAwardTypeAndPlanNameDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ResidentialMortgageBackedSecuritiesMember_9504ce3d-670d-4a2e-8ef8-ede03c018db7_terseLabel_en-US" xlink:label="lab_us-gaap_ResidentialMortgageBackedSecuritiesMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Residential mortgage-backed securities</link:label>
    <link:label id="lab_us-gaap_ResidentialMortgageBackedSecuritiesMember_label_en-US" xlink:label="lab_us-gaap_ResidentialMortgageBackedSecuritiesMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Residential Mortgage-Backed Securities [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ResidentialMortgageBackedSecuritiesMember" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ResidentialMortgageBackedSecuritiesMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ResidentialMortgageBackedSecuritiesMember" xlink:to="lab_us-gaap_ResidentialMortgageBackedSecuritiesMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ClassOfWarrantOrRightNumberOfSecuritiesCalledByWarrantsOrRights_5ef0e4c5-dc85-4fe9-bc07-d53e93e70098_terseLabel_en-US" xlink:label="lab_us-gaap_ClassOfWarrantOrRightNumberOfSecuritiesCalledByWarrantsOrRights" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Shares issued (in shares)</link:label>
    <link:label id="lab_us-gaap_ClassOfWarrantOrRightNumberOfSecuritiesCalledByWarrantsOrRights_label_en-US" xlink:label="lab_us-gaap_ClassOfWarrantOrRightNumberOfSecuritiesCalledByWarrantsOrRights" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Class of Warrant or Right, Number of Securities Called by Warrants or Rights</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ClassOfWarrantOrRightNumberOfSecuritiesCalledByWarrantsOrRights" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ClassOfWarrantOrRightNumberOfSecuritiesCalledByWarrantsOrRights"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ClassOfWarrantOrRightNumberOfSecuritiesCalledByWarrantsOrRights" xlink:to="lab_us-gaap_ClassOfWarrantOrRightNumberOfSecuritiesCalledByWarrantsOrRights" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EmployeeServiceShareBasedCompensationNonvestedAwardsTotalCompensationCostNotYetRecognizedPeriodForRecognition1_aa9b2759-4299-497c-a353-46eec7466a26_terseLabel_en-US" xlink:label="lab_us-gaap_EmployeeServiceShareBasedCompensationNonvestedAwardsTotalCompensationCostNotYetRecognizedPeriodForRecognition1" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Unrecognized compensation cost, period of recognition</link:label>
    <link:label id="lab_us-gaap_EmployeeServiceShareBasedCompensationNonvestedAwardsTotalCompensationCostNotYetRecognizedPeriodForRecognition1_label_en-US" xlink:label="lab_us-gaap_EmployeeServiceShareBasedCompensationNonvestedAwardsTotalCompensationCostNotYetRecognizedPeriodForRecognition1" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Share-Based Payment Arrangement, Nonvested Award, Cost Not yet Recognized, Period for Recognition</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EmployeeServiceShareBasedCompensationNonvestedAwardsTotalCompensationCostNotYetRecognizedPeriodForRecognition1" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_EmployeeServiceShareBasedCompensationNonvestedAwardsTotalCompensationCostNotYetRecognizedPeriodForRecognition1"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EmployeeServiceShareBasedCompensationNonvestedAwardsTotalCompensationCostNotYetRecognizedPeriodForRecognition1" xlink:to="lab_us-gaap_EmployeeServiceShareBasedCompensationNonvestedAwardsTotalCompensationCostNotYetRecognizedPeriodForRecognition1" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleUnrealizedLossPositionAccumulatedLoss_19687a04-5a8d-4779-8bb4-caf3483a3f8b_negatedTotalLabel_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleUnrealizedLossPositionAccumulatedLoss" xlink:role="http://www.xbrl.org/2009/role/negatedTotalLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Total, unrealized loss</link:label>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleUnrealizedLossPositionAccumulatedLoss_label_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleUnrealizedLossPositionAccumulatedLoss" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt Securities, Available-for-Sale, Unrealized Loss Position, Accumulated Loss</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtSecuritiesAvailableForSaleUnrealizedLossPositionAccumulatedLoss" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_DebtSecuritiesAvailableForSaleUnrealizedLossPositionAccumulatedLoss"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DebtSecuritiesAvailableForSaleUnrealizedLossPositionAccumulatedLoss" xlink:to="lab_us-gaap_DebtSecuritiesAvailableForSaleUnrealizedLossPositionAccumulatedLoss" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_RestructuringPlanDomain_2e8136bc-2d45-44f1-bdbc-2a901fceb754_terseLabel_en-US" xlink:label="lab_us-gaap_RestructuringPlanDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Restructuring Plan [Domain]</link:label>
    <link:label id="lab_us-gaap_RestructuringPlanDomain_label_en-US" xlink:label="lab_us-gaap_RestructuringPlanDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Restructuring Plan [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_RestructuringPlanDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_RestructuringPlanDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_RestructuringPlanDomain" xlink:to="lab_us-gaap_RestructuringPlanDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FairValueByBalanceSheetGroupingTextBlock_c3d23854-c85f-41db-b7a5-0829f23dd51d_terseLabel_en-US" xlink:label="lab_us-gaap_FairValueByBalanceSheetGroupingTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Schedule of Fair Value</link:label>
    <link:label id="lab_us-gaap_FairValueByBalanceSheetGroupingTextBlock_label_en-US" xlink:label="lab_us-gaap_FairValueByBalanceSheetGroupingTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Fair Value, by Balance Sheet Grouping [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueByBalanceSheetGroupingTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_FairValueByBalanceSheetGroupingTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FairValueByBalanceSheetGroupingTextBlock" xlink:to="lab_us-gaap_FairValueByBalanceSheetGroupingTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_EntityRegistrantName_eef169f0-2450-45ab-ad02-679b8ff7d39e_terseLabel_en-US" xlink:label="lab_dei_EntityRegistrantName" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Entity Registrant Name</link:label>
    <link:label id="lab_dei_EntityRegistrantName_label_en-US" xlink:label="lab_dei_EntityRegistrantName" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Entity Registrant Name</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_EntityRegistrantName" xlink:href="https://xbrl.sec.gov/dei/2022/dei-2022.xsd#dei_EntityRegistrantName"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_EntityRegistrantName" xlink:to="lab_dei_EntityRegistrantName" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_SubsequentEventsTextBlock_a4c2b3e2-e755-4b5c-b943-73e4d5b79c2d_terseLabel_en-US" xlink:label="lab_us-gaap_SubsequentEventsTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">SUBSEQUENT EVENTS</link:label>
    <link:label id="lab_us-gaap_SubsequentEventsTextBlock_label_en-US" xlink:label="lab_us-gaap_SubsequentEventsTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Subsequent Events [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SubsequentEventsTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_SubsequentEventsTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_SubsequentEventsTextBlock" xlink:to="lab_us-gaap_SubsequentEventsTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_InsuranceAbstract_label_en-US" xlink:label="lab_us-gaap_InsuranceAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Insurance [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_InsuranceAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_InsuranceAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_InsuranceAbstract" xlink:to="lab_us-gaap_InsuranceAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AccountsPayableAndAccruedLiabilitiesCurrentAndNoncurrent_067f6cd1-9558-4cf2-b30c-950174e8ea12_terseLabel_en-US" xlink:label="lab_us-gaap_AccountsPayableAndAccruedLiabilitiesCurrentAndNoncurrent" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Accounts payable and accrued expenses</link:label>
    <link:label id="lab_us-gaap_AccountsPayableAndAccruedLiabilitiesCurrentAndNoncurrent_label_en-US" xlink:label="lab_us-gaap_AccountsPayableAndAccruedLiabilitiesCurrentAndNoncurrent" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Accounts Payable and Accrued Liabilities</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AccountsPayableAndAccruedLiabilitiesCurrentAndNoncurrent" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_AccountsPayableAndAccruedLiabilitiesCurrentAndNoncurrent"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AccountsPayableAndAccruedLiabilitiesCurrentAndNoncurrent" xlink:to="lab_us-gaap_AccountsPayableAndAccruedLiabilitiesCurrentAndNoncurrent" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AdjustmentsToAdditionalPaidInCapitalSharebasedCompensationAndExerciseOfStockOptions_e3c8ce36-80a6-4e76-9e89-868274344ea2_terseLabel_en-US" xlink:label="lab_us-gaap_AdjustmentsToAdditionalPaidInCapitalSharebasedCompensationAndExerciseOfStockOptions" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Reclassification of early-exercised stock options from liabilities</link:label>
    <link:label id="lab_us-gaap_AdjustmentsToAdditionalPaidInCapitalSharebasedCompensationAndExerciseOfStockOptions_label_en-US" xlink:label="lab_us-gaap_AdjustmentsToAdditionalPaidInCapitalSharebasedCompensationAndExerciseOfStockOptions" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">APIC, Share-Based Payment Arrangement, Recognition and Exercise</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AdjustmentsToAdditionalPaidInCapitalSharebasedCompensationAndExerciseOfStockOptions" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_AdjustmentsToAdditionalPaidInCapitalSharebasedCompensationAndExerciseOfStockOptions"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AdjustmentsToAdditionalPaidInCapitalSharebasedCompensationAndExerciseOfStockOptions" xlink:to="lab_us-gaap_AdjustmentsToAdditionalPaidInCapitalSharebasedCompensationAndExerciseOfStockOptions" xlink:type="arc" order="1"/>
    <link:label id="lab_root_CovenantScenario1Member_f39d15d3-a772-4b17-bc42-80213de4e4ed_terseLabel_en-US" xlink:label="lab_root_CovenantScenario1Member" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Covenant Scenario 1</link:label>
    <link:label id="lab_root_CovenantScenario1Member_label_en-US" xlink:label="lab_root_CovenantScenario1Member" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Covenant Scenario 1 [Member]</link:label>
    <link:label id="lab_root_CovenantScenario1Member_documentation_en-US" xlink:label="lab_root_CovenantScenario1Member" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Covenant Scenario 1</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_root_CovenantScenario1Member" xlink:href="root-20220930.xsd#root_CovenantScenario1Member"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_root_CovenantScenario1Member" xlink:to="lab_root_CovenantScenario1Member" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_EntityAddressCityOrTown_140c3bcf-99b2-4c68-b00a-4bc944bb0cad_terseLabel_en-US" xlink:label="lab_dei_EntityAddressCityOrTown" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Entity Address, City or Town</link:label>
    <link:label id="lab_dei_EntityAddressCityOrTown_label_en-US" xlink:label="lab_dei_EntityAddressCityOrTown" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Entity Address, City or Town</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_EntityAddressCityOrTown" xlink:href="https://xbrl.sec.gov/dei/2022/dei-2022.xsd#dei_EntityAddressCityOrTown"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_EntityAddressCityOrTown" xlink:to="lab_dei_EntityAddressCityOrTown" xlink:type="arc" order="1"/>
    <link:label id="lab_root_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsAssumed_296590ed-3bd6-4741-b4a9-96ecdc3cae3b_terseLabel_en-US" xlink:label="lab_root_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsAssumed" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Assumed</link:label>
    <link:label id="lab_root_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsAssumed_label_en-US" xlink:label="lab_root_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsAssumed" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Liability For Unpaid Claims And Claims Adjustment Expense, Incurred Claims, Assumed</link:label>
    <link:label id="lab_root_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsAssumed_documentation_en-US" xlink:label="lab_root_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsAssumed" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Liability For Unpaid Claims And Claims Adjustment Expense, Incurred Claims, Assumed</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_root_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsAssumed" xlink:href="root-20220930.xsd#root_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsAssumed"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_root_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsAssumed" xlink:to="lab_root_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsAssumed" xlink:type="arc" order="1"/>
    <link:label id="lab_root_GrossWrittenPremiumsMember_2bbd8164-d7a5-4767-b4b4-cfab79f0b8d9_terseLabel_en-US" xlink:label="lab_root_GrossWrittenPremiumsMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Gross Written Premiums</link:label>
    <link:label id="lab_root_GrossWrittenPremiumsMember_label_en-US" xlink:label="lab_root_GrossWrittenPremiumsMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Gross Written Premiums [Member]</link:label>
    <link:label id="lab_root_GrossWrittenPremiumsMember_documentation_en-US" xlink:label="lab_root_GrossWrittenPremiumsMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Gross Written Premiums</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_root_GrossWrittenPremiumsMember" xlink:href="root-20220930.xsd#root_GrossWrittenPremiumsMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_root_GrossWrittenPremiumsMember" xlink:to="lab_root_GrossWrittenPremiumsMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_OperatingExpensesAbstract_b1bd4a3f-330a-4359-a4b4-80c90e66cab0_terseLabel_en-US" xlink:label="lab_us-gaap_OperatingExpensesAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Operating expenses:</link:label>
    <link:label id="lab_us-gaap_OperatingExpensesAbstract_label_en-US" xlink:label="lab_us-gaap_OperatingExpensesAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Operating Expenses [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OperatingExpensesAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_OperatingExpensesAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_OperatingExpensesAbstract" xlink:to="lab_us-gaap_OperatingExpensesAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ConsolidationPolicyTextBlock_65354f75-5f82-41ec-b3fd-9324c789f6f1_terseLabel_en-US" xlink:label="lab_us-gaap_ConsolidationPolicyTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Basis of Consolidation</link:label>
    <link:label id="lab_us-gaap_ConsolidationPolicyTextBlock_label_en-US" xlink:label="lab_us-gaap_ConsolidationPolicyTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Consolidation, Policy [Policy Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ConsolidationPolicyTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ConsolidationPolicyTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ConsolidationPolicyTextBlock" xlink:to="lab_us-gaap_ConsolidationPolicyTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_MinimumMember_a5b3fc0c-9885-4445-b6e7-ab2fbd324339_terseLabel_en-US" xlink:label="lab_srt_MinimumMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Minimum</link:label>
    <link:label id="lab_srt_MinimumMember_label_en-US" xlink:label="lab_srt_MinimumMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Minimum [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_MinimumMember" xlink:href="https://xbrl.fasb.org/srt/2022/elts/srt-2022.xsd#srt_MinimumMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_MinimumMember" xlink:to="lab_srt_MinimumMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesWithinOneYearAmortizedCost_090c7156-5346-4c98-b78c-f9848e9d088c_terseLabel_en-US" xlink:label="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesWithinOneYearAmortizedCost" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Due in one year or less</link:label>
    <link:label id="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesWithinOneYearAmortizedCost_label_en-US" xlink:label="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesWithinOneYearAmortizedCost" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt Securities, Available-for-Sale, Amortized Cost, Maturity, Allocated and Single Maturity Date, Year One</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesWithinOneYearAmortizedCost" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_AvailableForSaleSecuritiesDebtMaturitiesWithinOneYearAmortizedCost"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesWithinOneYearAmortizedCost" xlink:to="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesWithinOneYearAmortizedCost" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_StatementOfFinancialPositionAbstract_label_en-US" xlink:label="lab_us-gaap_StatementOfFinancialPositionAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Statement of Financial Position [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_StatementOfFinancialPositionAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_StatementOfFinancialPositionAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_StatementOfFinancialPositionAbstract" xlink:to="lab_us-gaap_StatementOfFinancialPositionAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_EntityEmergingGrowthCompany_ea1e47e1-210f-4f8d-a5b1-3e5cc621ba29_terseLabel_en-US" xlink:label="lab_dei_EntityEmergingGrowthCompany" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Entity Emerging Growth Company</link:label>
    <link:label id="lab_dei_EntityEmergingGrowthCompany_label_en-US" xlink:label="lab_dei_EntityEmergingGrowthCompany" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Entity Emerging Growth Company</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_EntityEmergingGrowthCompany" xlink:href="https://xbrl.sec.gov/dei/2022/dei-2022.xsd#dei_EntityEmergingGrowthCompany"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_EntityEmergingGrowthCompany" xlink:to="lab_dei_EntityEmergingGrowthCompany" xlink:type="arc" order="1"/>
    <link:label id="lab_root_DebtInstrumentCovenantComplianceAxis_e60b8391-0b8d-4072-b251-f342310d40d2_terseLabel_en-US" xlink:label="lab_root_DebtInstrumentCovenantComplianceAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt Instrument, Covenant Compliance [Axis]</link:label>
    <link:label id="lab_root_DebtInstrumentCovenantComplianceAxis_label_en-US" xlink:label="lab_root_DebtInstrumentCovenantComplianceAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt Instrument, Covenant Compliance [Axis]</link:label>
    <link:label id="lab_root_DebtInstrumentCovenantComplianceAxis_documentation_en-US" xlink:label="lab_root_DebtInstrumentCovenantComplianceAxis" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt Instrument, Covenant Compliance</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_root_DebtInstrumentCovenantComplianceAxis" xlink:href="root-20220930.xsd#root_DebtInstrumentCovenantComplianceAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_root_DebtInstrumentCovenantComplianceAxis" xlink:to="lab_root_DebtInstrumentCovenantComplianceAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CommonStockParOrStatedValuePerShare_d2548103-4264-465e-a404-0541cf1e3a58_terseLabel_en-US" xlink:label="lab_us-gaap_CommonStockParOrStatedValuePerShare" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Common stock, par value (in dollars per share)</link:label>
    <link:label id="lab_us-gaap_CommonStockParOrStatedValuePerShare_label_en-US" xlink:label="lab_us-gaap_CommonStockParOrStatedValuePerShare" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Common Stock, Par or Stated Value Per Share</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CommonStockParOrStatedValuePerShare" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_CommonStockParOrStatedValuePerShare"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CommonStockParOrStatedValuePerShare" xlink:to="lab_us-gaap_CommonStockParOrStatedValuePerShare" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CommitmentsAndContingenciesDisclosureAbstract_label_en-US" xlink:label="lab_us-gaap_CommitmentsAndContingenciesDisclosureAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Commitments and Contingencies Disclosure [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CommitmentsAndContingenciesDisclosureAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_CommitmentsAndContingenciesDisclosureAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CommitmentsAndContingenciesDisclosureAbstract" xlink:to="lab_us-gaap_CommitmentsAndContingenciesDisclosureAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_ScheduleOfEquityMethodInvestmentEquityMethodInvesteeNameAxis_09e5cde1-ec84-4ddf-adc6-7b8190cd49ad_terseLabel_en-US" xlink:label="lab_srt_ScheduleOfEquityMethodInvestmentEquityMethodInvesteeNameAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Investment, Name [Axis]</link:label>
    <link:label id="lab_srt_ScheduleOfEquityMethodInvestmentEquityMethodInvesteeNameAxis_label_en-US" xlink:label="lab_srt_ScheduleOfEquityMethodInvestmentEquityMethodInvesteeNameAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Investment, Name [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_ScheduleOfEquityMethodInvestmentEquityMethodInvesteeNameAxis" xlink:href="https://xbrl.fasb.org/srt/2022/elts/srt-2022.xsd#srt_ScheduleOfEquityMethodInvestmentEquityMethodInvesteeNameAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_ScheduleOfEquityMethodInvestmentEquityMethodInvesteeNameAxis" xlink:to="lab_srt_ScheduleOfEquityMethodInvestmentEquityMethodInvesteeNameAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FairValueDisclosuresTextBlock_13699862-f94f-43fa-b049-cdf321e45150_terseLabel_en-US" xlink:label="lab_us-gaap_FairValueDisclosuresTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">FAIR VALUE OF FINANCIAL INSTRUMENTS</link:label>
    <link:label id="lab_us-gaap_FairValueDisclosuresTextBlock_label_en-US" xlink:label="lab_us-gaap_FairValueDisclosuresTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Fair Value Disclosures [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueDisclosuresTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_FairValueDisclosuresTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FairValueDisclosuresTextBlock" xlink:to="lab_us-gaap_FairValueDisclosuresTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_TradingSymbol_bc11a0da-ca35-4c40-9ae9-d4b7b24e7dff_terseLabel_en-US" xlink:label="lab_dei_TradingSymbol" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Trading Symbol</link:label>
    <link:label id="lab_dei_TradingSymbol_label_en-US" xlink:label="lab_dei_TradingSymbol" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Trading Symbol</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_TradingSymbol" xlink:href="https://xbrl.sec.gov/dei/2022/dei-2022.xsd#dei_TradingSymbol"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_TradingSymbol" xlink:to="lab_dei_TradingSymbol" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_EntityFileNumber_feba1d9e-ff53-4312-8b32-55ca74f72e8b_terseLabel_en-US" xlink:label="lab_dei_EntityFileNumber" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Entity File Number</link:label>
    <link:label id="lab_dei_EntityFileNumber_label_en-US" xlink:label="lab_dei_EntityFileNumber" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Entity File Number</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_EntityFileNumber" xlink:href="https://xbrl.sec.gov/dei/2022/dei-2022.xsd#dei_EntityFileNumber"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_EntityFileNumber" xlink:to="lab_dei_EntityFileNumber" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AccumulatedOtherComprehensiveIncomeLossLineItems_a385a88b-9b06-4573-a245-e8b69c1c1726_terseLabel_en-US" xlink:label="lab_us-gaap_AccumulatedOtherComprehensiveIncomeLossLineItems" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Accumulated Other Comprehensive Income (Loss) [Line Items]</link:label>
    <link:label id="lab_us-gaap_AccumulatedOtherComprehensiveIncomeLossLineItems_label_en-US" xlink:label="lab_us-gaap_AccumulatedOtherComprehensiveIncomeLossLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Accumulated Other Comprehensive Income (Loss) [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AccumulatedOtherComprehensiveIncomeLossLineItems" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_AccumulatedOtherComprehensiveIncomeLossLineItems"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AccumulatedOtherComprehensiveIncomeLossLineItems" xlink:to="lab_us-gaap_AccumulatedOtherComprehensiveIncomeLossLineItems" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ScheduleOfInvestmentIncomeReportedAmountsByCategoryTable_5ac18b61-f25b-41d9-8a80-3996eea4d686_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfInvestmentIncomeReportedAmountsByCategoryTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Investment Income [Table]</link:label>
    <link:label id="lab_us-gaap_ScheduleOfInvestmentIncomeReportedAmountsByCategoryTable_label_en-US" xlink:label="lab_us-gaap_ScheduleOfInvestmentIncomeReportedAmountsByCategoryTable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Investment Income [Table]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfInvestmentIncomeReportedAmountsByCategoryTable" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ScheduleOfInvestmentIncomeReportedAmountsByCategoryTable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ScheduleOfInvestmentIncomeReportedAmountsByCategoryTable" xlink:to="lab_us-gaap_ScheduleOfInvestmentIncomeReportedAmountsByCategoryTable" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_EntityListingsTable_1b398bc8-3632-4a5e-a23d-7e845ea93d77_terseLabel_en-US" xlink:label="lab_dei_EntityListingsTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Entity Listings [Table]</link:label>
    <link:label id="lab_dei_EntityListingsTable_label_en-US" xlink:label="lab_dei_EntityListingsTable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Entity Listings [Table]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_EntityListingsTable" xlink:href="https://xbrl.sec.gov/dei/2022/dei-2022.xsd#dei_EntityListingsTable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_EntityListingsTable" xlink:to="lab_dei_EntityListingsTable" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_ExternalCreditRatingStandardPoorsMember_ead0354b-8638-4108-911e-549cd1a31662_terseLabel_en-US" xlink:label="lab_srt_ExternalCreditRatingStandardPoorsMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">External Credit Rating, Standard &amp; Poor's [Domain]</link:label>
    <link:label id="lab_srt_ExternalCreditRatingStandardPoorsMember_label_en-US" xlink:label="lab_srt_ExternalCreditRatingStandardPoorsMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">External Credit Rating, Standard &amp; Poor's [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_ExternalCreditRatingStandardPoorsMember" xlink:href="https://xbrl.fasb.org/srt/2022/elts/srt-2022.xsd#srt_ExternalCreditRatingStandardPoorsMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_ExternalCreditRatingStandardPoorsMember" xlink:to="lab_srt_ExternalCreditRatingStandardPoorsMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsGrantsInPeriod_450cee96-a7d9-438e-8908-d46dae79cbd5_terseLabel_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsGrantsInPeriod" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Granted (in shares)</link:label>
    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsGrantsInPeriod_label_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsGrantsInPeriod" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Share-Based Compensation Arrangement by Share-Based Payment Award, Equity Instruments Other than Options, Grants in Period</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsGrantsInPeriod" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsGrantsInPeriod"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsGrantsInPeriod" xlink:to="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsGrantsInPeriod" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_RestrictedStockUnitsRSUMember_1feb81d6-59d2-40ec-a397-ee7124594c69_terseLabel_en-US" xlink:label="lab_us-gaap_RestrictedStockUnitsRSUMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Restricted stock unit expense</link:label>
    <link:label id="lab_us-gaap_RestrictedStockUnitsRSUMember_ba07e378-804a-4f05-9224-767ffb540309_verboseLabel_en-US" xlink:label="lab_us-gaap_RestrictedStockUnitsRSUMember" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Restricted stock unit expense</link:label>
    <link:label id="lab_us-gaap_RestrictedStockUnitsRSUMember_73b20dd9-c920-4596-98e6-b725f357f9d6_netLabel_en-US" xlink:label="lab_us-gaap_RestrictedStockUnitsRSUMember" xlink:role="http://www.xbrl.org/2009/role/netLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Restricted stock units</link:label>
    <link:label id="lab_us-gaap_RestrictedStockUnitsRSUMember_label_en-US" xlink:label="lab_us-gaap_RestrictedStockUnitsRSUMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Restricted Stock Units (RSUs) [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_RestrictedStockUnitsRSUMember" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_RestrictedStockUnitsRSUMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_RestrictedStockUnitsRSUMember" xlink:to="lab_us-gaap_RestrictedStockUnitsRSUMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EffectiveIncomeTaxRateContinuingOperations_7720a598-82ea-4ea0-b794-983f9f127fcf_terseLabel_en-US" xlink:label="lab_us-gaap_EffectiveIncomeTaxRateContinuingOperations" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Effective income tax rate</link:label>
    <link:label id="lab_us-gaap_EffectiveIncomeTaxRateContinuingOperations_label_en-US" xlink:label="lab_us-gaap_EffectiveIncomeTaxRateContinuingOperations" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Effective Income Tax Rate Reconciliation, Percent</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EffectiveIncomeTaxRateContinuingOperations" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_EffectiveIncomeTaxRateContinuingOperations"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EffectiveIncomeTaxRateContinuingOperations" xlink:to="lab_us-gaap_EffectiveIncomeTaxRateContinuingOperations" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ConcentrationRiskByBenchmarkAxis_4d0977d9-7e5f-412f-ab09-92588f9353db_terseLabel_en-US" xlink:label="lab_us-gaap_ConcentrationRiskByBenchmarkAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Concentration Risk Benchmark [Axis]</link:label>
    <link:label id="lab_us-gaap_ConcentrationRiskByBenchmarkAxis_label_en-US" xlink:label="lab_us-gaap_ConcentrationRiskByBenchmarkAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Concentration Risk Benchmark [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ConcentrationRiskByBenchmarkAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ConcentrationRiskByBenchmarkAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ConcentrationRiskByBenchmarkAxis" xlink:to="lab_us-gaap_ConcentrationRiskByBenchmarkAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_UseOfEstimates_5baa5a4e-df45-4ac1-a457-122a5d39dc5b_terseLabel_en-US" xlink:label="lab_us-gaap_UseOfEstimates" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Use of Estimates</link:label>
    <link:label id="lab_us-gaap_UseOfEstimates_label_en-US" xlink:label="lab_us-gaap_UseOfEstimates" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Use of Estimates, Policy [Policy Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_UseOfEstimates" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_UseOfEstimates"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_UseOfEstimates" xlink:to="lab_us-gaap_UseOfEstimates" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CashAndCashEquivalentsFairValueDisclosure_731fd819-d3f9-488b-a472-50dfd2e2e9ff_terseLabel_en-US" xlink:label="lab_us-gaap_CashAndCashEquivalentsFairValueDisclosure" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Cash equivalents</link:label>
    <link:label id="lab_us-gaap_CashAndCashEquivalentsFairValueDisclosure_label_en-US" xlink:label="lab_us-gaap_CashAndCashEquivalentsFairValueDisclosure" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Cash and Cash Equivalents, Fair Value Disclosure</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CashAndCashEquivalentsFairValueDisclosure" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_CashAndCashEquivalentsFairValueDisclosure"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CashAndCashEquivalentsFairValueDisclosure" xlink:to="lab_us-gaap_CashAndCashEquivalentsFairValueDisclosure" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_OtherComprehensiveIncomeLossNetOfTaxPortionAttributableToParentAbstract_65b1e56c-77ed-422e-a766-861f45e2b397_terseLabel_en-US" xlink:label="lab_us-gaap_OtherComprehensiveIncomeLossNetOfTaxPortionAttributableToParentAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Other comprehensive loss:</link:label>
    <link:label id="lab_us-gaap_OtherComprehensiveIncomeLossNetOfTaxPortionAttributableToParentAbstract_label_en-US" xlink:label="lab_us-gaap_OtherComprehensiveIncomeLossNetOfTaxPortionAttributableToParentAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Other Comprehensive Income (Loss), Net of Tax, Portion Attributable to Parent [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OtherComprehensiveIncomeLossNetOfTaxPortionAttributableToParentAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_OtherComprehensiveIncomeLossNetOfTaxPortionAttributableToParentAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_OtherComprehensiveIncomeLossNetOfTaxPortionAttributableToParentAbstract" xlink:to="lab_us-gaap_OtherComprehensiveIncomeLossNetOfTaxPortionAttributableToParentAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AssumedPremiumsEarned_1e87e9ec-7425-4cb7-9a0b-61e0b11698eb_terseLabel_en-US" xlink:label="lab_us-gaap_AssumedPremiumsEarned" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Assumed</link:label>
    <link:label id="lab_us-gaap_AssumedPremiumsEarned_label_en-US" xlink:label="lab_us-gaap_AssumedPremiumsEarned" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Assumed Premiums Earned</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AssumedPremiumsEarned" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_AssumedPremiumsEarned"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AssumedPremiumsEarned" xlink:to="lab_us-gaap_AssumedPremiumsEarned" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ConcentrationRiskPercentage1_a7eee15e-3d45-4105-bd62-193b42ecd2a1_terseLabel_en-US" xlink:label="lab_us-gaap_ConcentrationRiskPercentage1" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Concentration percentage (in percent)</link:label>
    <link:label id="lab_us-gaap_ConcentrationRiskPercentage1_label_en-US" xlink:label="lab_us-gaap_ConcentrationRiskPercentage1" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Concentration Risk, Percentage</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ConcentrationRiskPercentage1" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ConcentrationRiskPercentage1"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ConcentrationRiskPercentage1" xlink:to="lab_us-gaap_ConcentrationRiskPercentage1" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_SubsequentEventsAbstract_label_en-US" xlink:label="lab_us-gaap_SubsequentEventsAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Subsequent Events [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SubsequentEventsAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_SubsequentEventsAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_SubsequentEventsAbstract" xlink:to="lab_us-gaap_SubsequentEventsAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_Revenues_3be0a7a5-4f58-4651-8081-07227a481d62_totalLabel_en-US" xlink:label="lab_us-gaap_Revenues" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Total revenues</link:label>
    <link:label id="lab_us-gaap_Revenues_label_en-US" xlink:label="lab_us-gaap_Revenues" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Revenues</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_Revenues" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_Revenues"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_Revenues" xlink:to="lab_us-gaap_Revenues" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleUnrealizedLossPositionFairValueTable_b136cc61-7f28-4de0-9c17-4fd25a17c09f_terseLabel_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleUnrealizedLossPositionFairValueTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt Securities, Available-for-sale, Unrealized Loss Position, Fair Value [Table]</link:label>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleUnrealizedLossPositionFairValueTable_label_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleUnrealizedLossPositionFairValueTable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt Securities, Available-for-Sale, Unrealized Loss Position, Fair Value [Table]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtSecuritiesAvailableForSaleUnrealizedLossPositionFairValueTable" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_DebtSecuritiesAvailableForSaleUnrealizedLossPositionFairValueTable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DebtSecuritiesAvailableForSaleUnrealizedLossPositionFairValueTable" xlink:to="lab_us-gaap_DebtSecuritiesAvailableForSaleUnrealizedLossPositionFairValueTable" xlink:type="arc" order="1"/>
    <link:label id="lab_root_RootReinsuranceCompanyLtdMember_7ab56116-68db-4fd2-a9a1-cf5c3fb1fa93_terseLabel_en-US" xlink:label="lab_root_RootReinsuranceCompanyLtdMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Root Reinsurance Company, Ltd.</link:label>
    <link:label id="lab_root_RootReinsuranceCompanyLtdMember_label_en-US" xlink:label="lab_root_RootReinsuranceCompanyLtdMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Root Reinsurance Company, Ltd. [Member]</link:label>
    <link:label id="lab_root_RootReinsuranceCompanyLtdMember_documentation_en-US" xlink:label="lab_root_RootReinsuranceCompanyLtdMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Root Reinsurance Company, Ltd.</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_root_RootReinsuranceCompanyLtdMember" xlink:href="root-20220930.xsd#root_RootReinsuranceCompanyLtdMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_root_RootReinsuranceCompanyLtdMember" xlink:to="lab_root_RootReinsuranceCompanyLtdMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_IncreaseDecreaseInAccountsPayableAndAccruedLiabilities_38dcd619-c447-4001-8a28-7027b496c80a_terseLabel_en-US" xlink:label="lab_us-gaap_IncreaseDecreaseInAccountsPayableAndAccruedLiabilities" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Accounts payable and accrued expenses</link:label>
    <link:label id="lab_us-gaap_IncreaseDecreaseInAccountsPayableAndAccruedLiabilities_label_en-US" xlink:label="lab_us-gaap_IncreaseDecreaseInAccountsPayableAndAccruedLiabilities" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Increase (Decrease) in Accounts Payable and Accrued Liabilities</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncreaseDecreaseInAccountsPayableAndAccruedLiabilities" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_IncreaseDecreaseInAccountsPayableAndAccruedLiabilities"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IncreaseDecreaseInAccountsPayableAndAccruedLiabilities" xlink:to="lab_us-gaap_IncreaseDecreaseInAccountsPayableAndAccruedLiabilities" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_IncomeTaxDisclosureTextBlock_8d561c6a-3aec-4c8f-8333-1b6781a81cdf_terseLabel_en-US" xlink:label="lab_us-gaap_IncomeTaxDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">INCOME TAXES</link:label>
    <link:label id="lab_us-gaap_IncomeTaxDisclosureTextBlock_label_en-US" xlink:label="lab_us-gaap_IncomeTaxDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Income Tax Disclosure [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncomeTaxDisclosureTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_IncomeTaxDisclosureTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IncomeTaxDisclosureTextBlock" xlink:to="lab_us-gaap_IncomeTaxDisclosureTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_root_A2020EquityIncentivePlanMember_f34c04d0-537e-48f0-8f20-22e263a590bb_terseLabel_en-US" xlink:label="lab_root_A2020EquityIncentivePlanMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">2020 Equity Incentive Plan</link:label>
    <link:label id="lab_root_A2020EquityIncentivePlanMember_label_en-US" xlink:label="lab_root_A2020EquityIncentivePlanMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">2020 Equity Incentive Plan [Member]</link:label>
    <link:label id="lab_root_A2020EquityIncentivePlanMember_documentation_en-US" xlink:label="lab_root_A2020EquityIncentivePlanMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">2020 Equity Incentive Plan</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_root_A2020EquityIncentivePlanMember" xlink:href="root-20220930.xsd#root_A2020EquityIncentivePlanMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_root_A2020EquityIncentivePlanMember" xlink:to="lab_root_A2020EquityIncentivePlanMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPosition12MonthsOrLonger_bda411b2-230a-469b-bd44-17e4a1b0c357_terseLabel_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPosition12MonthsOrLonger" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">12 months or more, fair value</link:label>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPosition12MonthsOrLonger_label_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPosition12MonthsOrLonger" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt Securities, Available-for-Sale, Continuous Unrealized Loss Position, 12 Months or Longer</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPosition12MonthsOrLonger" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPosition12MonthsOrLonger"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPosition12MonthsOrLonger" xlink:to="lab_us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPosition12MonthsOrLonger" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ClassOfWarrantOrRightExercisePriceOfWarrantsOrRights1_ebde33a9-adcb-4a28-8708-72262a06d472_terseLabel_en-US" xlink:label="lab_us-gaap_ClassOfWarrantOrRightExercisePriceOfWarrantsOrRights1" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Exercise price (in dollars per share)</link:label>
    <link:label id="lab_us-gaap_ClassOfWarrantOrRightExercisePriceOfWarrantsOrRights1_label_en-US" xlink:label="lab_us-gaap_ClassOfWarrantOrRightExercisePriceOfWarrantsOrRights1" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Class of Warrant or Right, Exercise Price of Warrants or Rights</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ClassOfWarrantOrRightExercisePriceOfWarrantsOrRights1" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ClassOfWarrantOrRightExercisePriceOfWarrantsOrRights1"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ClassOfWarrantOrRightExercisePriceOfWarrantsOrRights1" xlink:to="lab_us-gaap_ClassOfWarrantOrRightExercisePriceOfWarrantsOrRights1" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EarningsPerShareBasic_8776f8b6-ee77-43a6-823f-206d556b7713_terseLabel_en-US" xlink:label="lab_us-gaap_EarningsPerShareBasic" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Loss per common share: basic (both Class A and B) (in dollars per share)</link:label>
    <link:label id="lab_us-gaap_EarningsPerShareBasic_label_en-US" xlink:label="lab_us-gaap_EarningsPerShareBasic" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Earnings Per Share, Basic</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EarningsPerShareBasic" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_EarningsPerShareBasic"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EarningsPerShareBasic" xlink:to="lab_us-gaap_EarningsPerShareBasic" xlink:type="arc" order="1"/>
    <link:label id="lab_root_CovenantScenario2Member_7d7ddc69-a443-42c2-951b-9951be246080_terseLabel_en-US" xlink:label="lab_root_CovenantScenario2Member" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Covenant Scenario 2</link:label>
    <link:label id="lab_root_CovenantScenario2Member_label_en-US" xlink:label="lab_root_CovenantScenario2Member" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Covenant Scenario 2 [Member]</link:label>
    <link:label id="lab_root_CovenantScenario2Member_documentation_en-US" xlink:label="lab_root_CovenantScenario2Member" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Covenant Scenario 2</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_root_CovenantScenario2Member" xlink:href="root-20220930.xsd#root_CovenantScenario2Member"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_root_CovenantScenario2Member" xlink:to="lab_root_CovenantScenario2Member" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ScheduleOfEquityMethodInvestmentsTable_ed9aef5f-86da-4015-b5be-463f98cb79a5_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfEquityMethodInvestmentsTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Schedule of Equity Method Investments [Table]</link:label>
    <link:label id="lab_us-gaap_ScheduleOfEquityMethodInvestmentsTable_label_en-US" xlink:label="lab_us-gaap_ScheduleOfEquityMethodInvestmentsTable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Schedule of Equity Method Investments [Table]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfEquityMethodInvestmentsTable" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ScheduleOfEquityMethodInvestmentsTable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ScheduleOfEquityMethodInvestmentsTable" xlink:to="lab_us-gaap_ScheduleOfEquityMethodInvestmentsTable" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_InsuranceDisclosureTextBlock_68efc304-9b49-44d5-a001-9d584d8e79b5_terseLabel_en-US" xlink:label="lab_us-gaap_InsuranceDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">LOSS AND LOSS ADJUSTMENT EXPENSE RESERVES</link:label>
    <link:label id="lab_us-gaap_InsuranceDisclosureTextBlock_label_en-US" xlink:label="lab_us-gaap_InsuranceDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Insurance Disclosure [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_InsuranceDisclosureTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_InsuranceDisclosureTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_InsuranceDisclosureTextBlock" xlink:to="lab_us-gaap_InsuranceDisclosureTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ConcentrationRiskTypeDomain_2ccbfdc1-c1e7-4fcf-8d3a-dd91e0494758_terseLabel_en-US" xlink:label="lab_us-gaap_ConcentrationRiskTypeDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Concentration Risk Type [Domain]</link:label>
    <link:label id="lab_us-gaap_ConcentrationRiskTypeDomain_label_en-US" xlink:label="lab_us-gaap_ConcentrationRiskTypeDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Concentration Risk Type [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ConcentrationRiskTypeDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ConcentrationRiskTypeDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ConcentrationRiskTypeDomain" xlink:to="lab_us-gaap_ConcentrationRiskTypeDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_RepurchaseAgreementCounterpartyNameDomain_d2d26881-0322-4826-bba5-4e49d028b7c5_terseLabel_en-US" xlink:label="lab_srt_RepurchaseAgreementCounterpartyNameDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Counterparty Name [Domain]</link:label>
    <link:label id="lab_srt_RepurchaseAgreementCounterpartyNameDomain_label_en-US" xlink:label="lab_srt_RepurchaseAgreementCounterpartyNameDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Counterparty Name [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_RepurchaseAgreementCounterpartyNameDomain" xlink:href="https://xbrl.fasb.org/srt/2022/elts/srt-2022.xsd#srt_RepurchaseAgreementCounterpartyNameDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_RepurchaseAgreementCounterpartyNameDomain" xlink:to="lab_srt_RepurchaseAgreementCounterpartyNameDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_TreasuryStockMember_28605d07-64ab-4579-b4f5-e34068d7a5b3_terseLabel_en-US" xlink:label="lab_us-gaap_TreasuryStockMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Treasury Stock</link:label>
    <link:label id="lab_us-gaap_TreasuryStockMember_label_en-US" xlink:label="lab_us-gaap_TreasuryStockMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Treasury Stock [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_TreasuryStockMember" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_TreasuryStockMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_TreasuryStockMember" xlink:to="lab_us-gaap_TreasuryStockMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_SellingAndMarketingExpense_9c19fb10-3ce6-4e12-a97f-ed903933b536_terseLabel_en-US" xlink:label="lab_us-gaap_SellingAndMarketingExpense" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Sales and marketing</link:label>
    <link:label id="lab_us-gaap_SellingAndMarketingExpense_label_en-US" xlink:label="lab_us-gaap_SellingAndMarketingExpense" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Selling and Marketing Expense</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SellingAndMarketingExpense" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_SellingAndMarketingExpense"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_SellingAndMarketingExpense" xlink:to="lab_us-gaap_SellingAndMarketingExpense" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_StockholdersEquity_7e78eb4a-46ea-4623-92ca-b8c92179d6f9_totalLabel_en-US" xlink:label="lab_us-gaap_StockholdersEquity" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Total stockholders&#8217; equity</link:label>
    <link:label id="lab_us-gaap_StockholdersEquity_8b04a7d8-7168-4a2b-b76a-3391e21ca4e9_periodStartLabel_en-US" xlink:label="lab_us-gaap_StockholdersEquity" xlink:role="http://www.xbrl.org/2003/role/periodStartLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Beginning balance</link:label>
    <link:label id="lab_us-gaap_StockholdersEquity_33ec5d9a-fb41-4976-b282-c0758af6d143_periodEndLabel_en-US" xlink:label="lab_us-gaap_StockholdersEquity" xlink:role="http://www.xbrl.org/2003/role/periodEndLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Ending balance</link:label>
    <link:label id="lab_us-gaap_StockholdersEquity_label_en-US" xlink:label="lab_us-gaap_StockholdersEquity" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Stockholders' Equity Attributable to Parent</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_StockholdersEquity" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_StockholdersEquity"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_StockholdersEquity" xlink:to="lab_us-gaap_StockholdersEquity" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsForfeituresWeightedAverageGrantDateFairValue_2ad624ea-1632-4f37-8cb5-8cde15617e46_terseLabel_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsForfeituresWeightedAverageGrantDateFairValue" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Forfeited, expired or canceled, weighted-average grant date fair value (in dollars per share)</link:label>
    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsForfeituresWeightedAverageGrantDateFairValue_label_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsForfeituresWeightedAverageGrantDateFairValue" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Share-Based Compensation Arrangement by Share-Based Payment Award, Equity Instruments Other than Options, Forfeitures, Weighted Average Grant Date Fair Value</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsForfeituresWeightedAverageGrantDateFairValue" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsForfeituresWeightedAverageGrantDateFairValue"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsForfeituresWeightedAverageGrantDateFairValue" xlink:to="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsForfeituresWeightedAverageGrantDateFairValue" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterFiveThroughTenYearsAmortizedCost_8687ab22-591d-49fd-8500-e3cb5efbdd8f_terseLabel_en-US" xlink:label="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterFiveThroughTenYearsAmortizedCost" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Due five years through 10 years</link:label>
    <link:label id="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterFiveThroughTenYearsAmortizedCost_label_en-US" xlink:label="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterFiveThroughTenYearsAmortizedCost" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt Securities, Available-for-Sale, Amortized Cost, Maturity, Allocated and Single Maturity Date, after Year 5 Through 10</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterFiveThroughTenYearsAmortizedCost" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterFiveThroughTenYearsAmortizedCost"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterFiveThroughTenYearsAmortizedCost" xlink:to="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterFiveThroughTenYearsAmortizedCost" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_VestingDomain_7d62c7e2-6b4a-4b91-a07e-6d3cf673ac9f_terseLabel_en-US" xlink:label="lab_us-gaap_VestingDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Vesting [Domain]</link:label>
    <link:label id="lab_us-gaap_VestingDomain_label_en-US" xlink:label="lab_us-gaap_VestingDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Vesting [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_VestingDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_VestingDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_VestingDomain" xlink:to="lab_us-gaap_VestingDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleAllowanceForCreditLoss_2d6e1ae6-e43b-41b7-b1f3-010ac1135ceb_terseLabel_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleAllowanceForCreditLoss" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Allowance for Expected Credit Losses</link:label>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleAllowanceForCreditLoss_label_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleAllowanceForCreditLoss" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt Securities, Available-for-Sale, Allowance for Credit Loss</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtSecuritiesAvailableForSaleAllowanceForCreditLoss" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_DebtSecuritiesAvailableForSaleAllowanceForCreditLoss"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DebtSecuritiesAvailableForSaleAllowanceForCreditLoss" xlink:to="lab_us-gaap_DebtSecuritiesAvailableForSaleAllowanceForCreditLoss" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_EntityInteractiveDataCurrent_a2746bb9-acab-403c-88f1-7fd050f32293_terseLabel_en-US" xlink:label="lab_dei_EntityInteractiveDataCurrent" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Entity Interactive Data Current</link:label>
    <link:label id="lab_dei_EntityInteractiveDataCurrent_label_en-US" xlink:label="lab_dei_EntityInteractiveDataCurrent" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Entity Interactive Data Current</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_EntityInteractiveDataCurrent" xlink:href="https://xbrl.sec.gov/dei/2022/dei-2022.xsd#dei_EntityInteractiveDataCurrent"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_EntityInteractiveDataCurrent" xlink:to="lab_dei_EntityInteractiveDataCurrent" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CommercialMortgageBackedSecuritiesMember_e2ea6c30-12fd-46ad-a18a-732992a8edb6_terseLabel_en-US" xlink:label="lab_us-gaap_CommercialMortgageBackedSecuritiesMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Commercial mortgage backed securities</link:label>
    <link:label id="lab_us-gaap_CommercialMortgageBackedSecuritiesMember_label_en-US" xlink:label="lab_us-gaap_CommercialMortgageBackedSecuritiesMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Commercial Mortgage-Backed Securities [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CommercialMortgageBackedSecuritiesMember" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_CommercialMortgageBackedSecuritiesMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CommercialMortgageBackedSecuritiesMember" xlink:to="lab_us-gaap_CommercialMortgageBackedSecuritiesMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FairValueByBalanceSheetGroupingTable_d8a9416b-30f2-4897-8705-9b682ae6fba6_terseLabel_en-US" xlink:label="lab_us-gaap_FairValueByBalanceSheetGroupingTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Fair Value, by Balance Sheet Grouping [Table]</link:label>
    <link:label id="lab_us-gaap_FairValueByBalanceSheetGroupingTable_label_en-US" xlink:label="lab_us-gaap_FairValueByBalanceSheetGroupingTable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Fair Value, by Balance Sheet Grouping [Table]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueByBalanceSheetGroupingTable" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_FairValueByBalanceSheetGroupingTable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FairValueByBalanceSheetGroupingTable" xlink:to="lab_us-gaap_FairValueByBalanceSheetGroupingTable" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CededPremiumsEarned_8dcd7961-6657-48d4-9d34-9991a8478be2_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_CededPremiumsEarned" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Ceded</link:label>
    <link:label id="lab_us-gaap_CededPremiumsEarned_label_en-US" xlink:label="lab_us-gaap_CededPremiumsEarned" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Ceded Premiums Earned</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CededPremiumsEarned" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_CededPremiumsEarned"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CededPremiumsEarned" xlink:to="lab_us-gaap_CededPremiumsEarned" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_IncreaseDecreaseInOperatingCapitalAbstract_4ffc3b75-d1d5-4a2a-9b80-daa7977f9939_terseLabel_en-US" xlink:label="lab_us-gaap_IncreaseDecreaseInOperatingCapitalAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Changes in operating assets and liabilities:</link:label>
    <link:label id="lab_us-gaap_IncreaseDecreaseInOperatingCapitalAbstract_label_en-US" xlink:label="lab_us-gaap_IncreaseDecreaseInOperatingCapitalAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Increase (Decrease) in Operating Capital [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncreaseDecreaseInOperatingCapitalAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_IncreaseDecreaseInOperatingCapitalAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IncreaseDecreaseInOperatingCapitalAbstract" xlink:to="lab_us-gaap_IncreaseDecreaseInOperatingCapitalAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ProceedsFromSaleOfAvailableForSaleSecuritiesDebt_626bc335-9ac2-46c0-8dab-572ff94fa9ef_terseLabel_en-US" xlink:label="lab_us-gaap_ProceedsFromSaleOfAvailableForSaleSecuritiesDebt" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Sales of investments</link:label>
    <link:label id="lab_us-gaap_ProceedsFromSaleOfAvailableForSaleSecuritiesDebt_label_en-US" xlink:label="lab_us-gaap_ProceedsFromSaleOfAvailableForSaleSecuritiesDebt" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Proceeds from Sale of Debt Securities, Available-for-Sale</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ProceedsFromSaleOfAvailableForSaleSecuritiesDebt" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ProceedsFromSaleOfAvailableForSaleSecuritiesDebt"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ProceedsFromSaleOfAvailableForSaleSecuritiesDebt" xlink:to="lab_us-gaap_ProceedsFromSaleOfAvailableForSaleSecuritiesDebt" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_PortionAtFairValueFairValueDisclosureMember_24469d34-b5ee-4022-bc78-5ae6e7aa776b_terseLabel_en-US" xlink:label="lab_us-gaap_PortionAtFairValueFairValueDisclosureMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Portion at Fair Value Measurement</link:label>
    <link:label id="lab_us-gaap_PortionAtFairValueFairValueDisclosureMember_label_en-US" xlink:label="lab_us-gaap_PortionAtFairValueFairValueDisclosureMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Portion at Fair Value Measurement [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PortionAtFairValueFairValueDisclosureMember" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_PortionAtFairValueFairValueDisclosureMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PortionAtFairValueFairValueDisclosureMember" xlink:to="lab_us-gaap_PortionAtFairValueFairValueDisclosureMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_RetainedEarningsMember_12bb58fc-ad4c-45df-acc7-e6395efd62c4_terseLabel_en-US" xlink:label="lab_us-gaap_RetainedEarningsMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Accumulated Loss</link:label>
    <link:label id="lab_us-gaap_RetainedEarningsMember_label_en-US" xlink:label="lab_us-gaap_RetainedEarningsMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Retained Earnings [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_RetainedEarningsMember" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_RetainedEarningsMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_RetainedEarningsMember" xlink:to="lab_us-gaap_RetainedEarningsMember" xlink:type="arc" order="1"/>
    <link:label id="lab_stpr_GA_fee46e0d-7d32-4987-a110-61b4c1c761cb_terseLabel_en-US" xlink:label="lab_stpr_GA" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Georgia</link:label>
    <link:label id="lab_stpr_GA_label_en-US" xlink:label="lab_stpr_GA" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">GEORGIA</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_stpr_GA" xlink:href="https://xbrl.sec.gov/stpr/2022/stpr-2022.xsd#stpr_GA"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_stpr_GA" xlink:to="lab_stpr_GA" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EmployeeServiceShareBasedCompensationNonvestedAwardsTotalCompensationCostNotYetRecognizedStockOptions_5756c75d-b7b3-4ccc-8841-3cb9fe88a537_terseLabel_en-US" xlink:label="lab_us-gaap_EmployeeServiceShareBasedCompensationNonvestedAwardsTotalCompensationCostNotYetRecognizedStockOptions" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Unrecognized compensation cost, options</link:label>
    <link:label id="lab_us-gaap_EmployeeServiceShareBasedCompensationNonvestedAwardsTotalCompensationCostNotYetRecognizedStockOptions_label_en-US" xlink:label="lab_us-gaap_EmployeeServiceShareBasedCompensationNonvestedAwardsTotalCompensationCostNotYetRecognizedStockOptions" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Share-Based Payment Arrangement, Nonvested Award, Option, Cost Not yet Recognized, Amount</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EmployeeServiceShareBasedCompensationNonvestedAwardsTotalCompensationCostNotYetRecognizedStockOptions" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_EmployeeServiceShareBasedCompensationNonvestedAwardsTotalCompensationCostNotYetRecognizedStockOptions"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EmployeeServiceShareBasedCompensationNonvestedAwardsTotalCompensationCostNotYetRecognizedStockOptions" xlink:to="lab_us-gaap_EmployeeServiceShareBasedCompensationNonvestedAwardsTotalCompensationCostNotYetRecognizedStockOptions" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CommonStockMember_c15fbf14-3241-4ae8-8050-31bf557767d1_verboseLabel_en-US" xlink:label="lab_us-gaap_CommonStockMember" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Class A and Class B Common Stock(1)</link:label>
    <link:label id="lab_us-gaap_CommonStockMember_label_en-US" xlink:label="lab_us-gaap_CommonStockMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Common Stock [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CommonStockMember" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_CommonStockMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CommonStockMember" xlink:to="lab_us-gaap_CommonStockMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ScheduleOfEmployeeServiceShareBasedCompensationAllocationOfRecognizedPeriodCostsTextBlock_e2c0c644-f197-4b17-af5d-8b63fcf80a11_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfEmployeeServiceShareBasedCompensationAllocationOfRecognizedPeriodCostsTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Schedule of Share-Based Compensation Expense</link:label>
    <link:label id="lab_us-gaap_ScheduleOfEmployeeServiceShareBasedCompensationAllocationOfRecognizedPeriodCostsTextBlock_label_en-US" xlink:label="lab_us-gaap_ScheduleOfEmployeeServiceShareBasedCompensationAllocationOfRecognizedPeriodCostsTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Share-Based Payment Arrangement, Expensed and Capitalized, Amount [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfEmployeeServiceShareBasedCompensationAllocationOfRecognizedPeriodCostsTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ScheduleOfEmployeeServiceShareBasedCompensationAllocationOfRecognizedPeriodCostsTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ScheduleOfEmployeeServiceShareBasedCompensationAllocationOfRecognizedPeriodCostsTextBlock" xlink:to="lab_us-gaap_ScheduleOfEmployeeServiceShareBasedCompensationAllocationOfRecognizedPeriodCostsTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_OtherComprehensiveIncomeLossNetOfTaxPortionAttributableToParent_f55f3fa4-e4f0-4b14-9a8b-b8111147e984_verboseLabel_en-US" xlink:label="lab_us-gaap_OtherComprehensiveIncomeLossNetOfTaxPortionAttributableToParent" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Other comprehensive loss</link:label>
    <link:label id="lab_us-gaap_OtherComprehensiveIncomeLossNetOfTaxPortionAttributableToParent_379e7eeb-4c6f-45e6-a7fd-5f1085fe6c19_totalLabel_en-US" xlink:label="lab_us-gaap_OtherComprehensiveIncomeLossNetOfTaxPortionAttributableToParent" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Other comprehensive loss</link:label>
    <link:label id="lab_us-gaap_OtherComprehensiveIncomeLossNetOfTaxPortionAttributableToParent_label_en-US" xlink:label="lab_us-gaap_OtherComprehensiveIncomeLossNetOfTaxPortionAttributableToParent" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Other Comprehensive Income (Loss), Net of Tax, Portion Attributable to Parent</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OtherComprehensiveIncomeLossNetOfTaxPortionAttributableToParent" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_OtherComprehensiveIncomeLossNetOfTaxPortionAttributableToParent"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_OtherComprehensiveIncomeLossNetOfTaxPortionAttributableToParent" xlink:to="lab_us-gaap_OtherComprehensiveIncomeLossNetOfTaxPortionAttributableToParent" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_OciBeforeReclassificationsNetOfTaxAttributableToParent_cd60afb5-278f-4e76-aa3c-37b1aeac7de8_terseLabel_en-US" xlink:label="lab_us-gaap_OciBeforeReclassificationsNetOfTaxAttributableToParent" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Other comprehensive loss before reclassifications</link:label>
    <link:label id="lab_us-gaap_OciBeforeReclassificationsNetOfTaxAttributableToParent_label_en-US" xlink:label="lab_us-gaap_OciBeforeReclassificationsNetOfTaxAttributableToParent" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">OCI, before Reclassifications, Net of Tax, Attributable to Parent</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OciBeforeReclassificationsNetOfTaxAttributableToParent" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_OciBeforeReclassificationsNetOfTaxAttributableToParent"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_OciBeforeReclassificationsNetOfTaxAttributableToParent" xlink:to="lab_us-gaap_OciBeforeReclassificationsNetOfTaxAttributableToParent" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_PremiumsReceivableAtCarryingValue_18a2fe86-0aef-451f-a1f8-e495d3863445_terseLabel_en-US" xlink:label="lab_us-gaap_PremiumsReceivableAtCarryingValue" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Premiums receivable, net of allowance of $3.3 and $5.4 at September&#160;30, 2022 and December&#160;31, 2021, respectively</link:label>
    <link:label id="lab_us-gaap_PremiumsReceivableAtCarryingValue_label_en-US" xlink:label="lab_us-gaap_PremiumsReceivableAtCarryingValue" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Premiums Receivable, Net</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PremiumsReceivableAtCarryingValue" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_PremiumsReceivableAtCarryingValue"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PremiumsReceivableAtCarryingValue" xlink:to="lab_us-gaap_PremiumsReceivableAtCarryingValue" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardNumberOfSharesAvailableForGrant_b89232b6-0cb6-4c25-ae26-8bfd583dcc52_terseLabel_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardNumberOfSharesAvailableForGrant" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Shares available for issuance (in shares)</link:label>
    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardNumberOfSharesAvailableForGrant_label_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardNumberOfSharesAvailableForGrant" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Share-Based Compensation Arrangement by Share-Based Payment Award, Number of Shares Available for Grant</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardNumberOfSharesAvailableForGrant" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardNumberOfSharesAvailableForGrant"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardNumberOfSharesAvailableForGrant" xlink:to="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardNumberOfSharesAvailableForGrant" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_StatementClassOfStockAxis_d8bd4f58-44a0-4e4c-801f-5fc298b3216b_terseLabel_en-US" xlink:label="lab_us-gaap_StatementClassOfStockAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Class of Stock [Axis]</link:label>
    <link:label id="lab_us-gaap_StatementClassOfStockAxis_label_en-US" xlink:label="lab_us-gaap_StatementClassOfStockAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Class of Stock [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_StatementClassOfStockAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_StatementClassOfStockAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_StatementClassOfStockAxis" xlink:to="lab_us-gaap_StatementClassOfStockAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ScheduleOfNonvestedRestrictedStockUnitsActivityTableTextBlock_43581b0c-1ec0-4cbd-9ab3-b0036a4da53f_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfNonvestedRestrictedStockUnitsActivityTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Summary of RSU Activity</link:label>
    <link:label id="lab_us-gaap_ScheduleOfNonvestedRestrictedStockUnitsActivityTableTextBlock_label_en-US" xlink:label="lab_us-gaap_ScheduleOfNonvestedRestrictedStockUnitsActivityTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Schedule of Nonvested Restricted Stock Units Activity [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfNonvestedRestrictedStockUnitsActivityTableTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ScheduleOfNonvestedRestrictedStockUnitsActivityTableTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ScheduleOfNonvestedRestrictedStockUnitsActivityTableTextBlock" xlink:to="lab_us-gaap_ScheduleOfNonvestedRestrictedStockUnitsActivityTableTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_StatementTable_8133a1b5-e6c7-4ffd-8250-5ed6c81bfe87_terseLabel_en-US" xlink:label="lab_us-gaap_StatementTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Statement [Table]</link:label>
    <link:label id="lab_us-gaap_StatementTable_label_en-US" xlink:label="lab_us-gaap_StatementTable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Statement [Table]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_StatementTable" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_StatementTable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_StatementTable" xlink:to="lab_us-gaap_StatementTable" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_PremiumReceivableCreditLossExpenseReversal_254d778a-25fc-4cac-ba0c-bcd124850a4c_terseLabel_en-US" xlink:label="lab_us-gaap_PremiumReceivableCreditLossExpenseReversal" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Bad debt expense</link:label>
    <link:label id="lab_us-gaap_PremiumReceivableCreditLossExpenseReversal_label_en-US" xlink:label="lab_us-gaap_PremiumReceivableCreditLossExpenseReversal" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Premium Receivable, Credit Loss Expense (Reversal)</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PremiumReceivableCreditLossExpenseReversal" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_PremiumReceivableCreditLossExpenseReversal"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PremiumReceivableCreditLossExpenseReversal" xlink:to="lab_us-gaap_PremiumReceivableCreditLossExpenseReversal" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsVestedInPeriodWeightedAverageGrantDateFairValue_3daf8315-f2d2-478a-aed0-8d38789c687b_terseLabel_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsVestedInPeriodWeightedAverageGrantDateFairValue" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Vested, weighted-average grant date fair value (in dollars per share)</link:label>
    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsVestedInPeriodWeightedAverageGrantDateFairValue_label_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsVestedInPeriodWeightedAverageGrantDateFairValue" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Share-Based Compensation Arrangement by Share-Based Payment Award, Equity Instruments Other than Options, Vested in Period, Weighted Average Grant Date Fair Value</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsVestedInPeriodWeightedAverageGrantDateFairValue" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsVestedInPeriodWeightedAverageGrantDateFairValue"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsVestedInPeriodWeightedAverageGrantDateFairValue" xlink:to="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsVestedInPeriodWeightedAverageGrantDateFairValue" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_DocumentQuarterlyReport_37d758ba-b5a7-4600-8236-9f21d9d18827_terseLabel_en-US" xlink:label="lab_dei_DocumentQuarterlyReport" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Document Quarterly Report</link:label>
    <link:label id="lab_dei_DocumentQuarterlyReport_label_en-US" xlink:label="lab_dei_DocumentQuarterlyReport" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Document Quarterly Report</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_DocumentQuarterlyReport" xlink:href="https://xbrl.sec.gov/dei/2022/dei-2022.xsd#dei_DocumentQuarterlyReport"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_DocumentQuarterlyReport" xlink:to="lab_dei_DocumentQuarterlyReport" xlink:type="arc" order="1"/>
    <link:label id="lab_root_TermLoanCMember_0d3c0c46-78c4-4561-ae8b-9e87a444f511_terseLabel_en-US" xlink:label="lab_root_TermLoanCMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Term Loan</link:label>
    <link:label id="lab_root_TermLoanCMember_label_en-US" xlink:label="lab_root_TermLoanCMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Term Loan C [Member]</link:label>
    <link:label id="lab_root_TermLoanCMember_documentation_en-US" xlink:label="lab_root_TermLoanCMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Term Loan C</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_root_TermLoanCMember" xlink:href="root-20220930.xsd#root_TermLoanCMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_root_TermLoanCMember" xlink:to="lab_root_TermLoanCMember" xlink:type="arc" order="1"/>
    <link:label id="lab_root_TechnologyAndDevelopmentExpenseMember_0518cb0b-3506-409a-af9e-a04be866261c_terseLabel_en-US" xlink:label="lab_root_TechnologyAndDevelopmentExpenseMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Technology and development</link:label>
    <link:label id="lab_root_TechnologyAndDevelopmentExpenseMember_label_en-US" xlink:label="lab_root_TechnologyAndDevelopmentExpenseMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Technology And Development Expense [Member]</link:label>
    <link:label id="lab_root_TechnologyAndDevelopmentExpenseMember_documentation_en-US" xlink:label="lab_root_TechnologyAndDevelopmentExpenseMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Technology And Development Expense</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_root_TechnologyAndDevelopmentExpenseMember" xlink:href="root-20220930.xsd#root_TechnologyAndDevelopmentExpenseMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_root_TechnologyAndDevelopmentExpenseMember" xlink:to="lab_root_TechnologyAndDevelopmentExpenseMember" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_RangeAxis_6d47875d-0875-4a8e-9abd-09352b5a3c35_terseLabel_en-US" xlink:label="lab_srt_RangeAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Statistical Measurement [Axis]</link:label>
    <link:label id="lab_srt_RangeAxis_label_en-US" xlink:label="lab_srt_RangeAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Statistical Measurement [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_RangeAxis" xlink:href="https://xbrl.fasb.org/srt/2022/elts/srt-2022.xsd#srt_RangeAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_RangeAxis" xlink:to="lab_srt_RangeAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_root_AllOtherStatesMember_59bb96d5-d534-4285-a5f1-4d9d5ab2f824_terseLabel_en-US" xlink:label="lab_root_AllOtherStatesMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">All others states</link:label>
    <link:label id="lab_root_AllOtherStatesMember_label_en-US" xlink:label="lab_root_AllOtherStatesMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">All Other States [Member]</link:label>
    <link:label id="lab_root_AllOtherStatesMember_documentation_en-US" xlink:label="lab_root_AllOtherStatesMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">All Other States</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_root_AllOtherStatesMember" xlink:href="root-20220930.xsd#root_AllOtherStatesMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_root_AllOtherStatesMember" xlink:to="lab_root_AllOtherStatesMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_RetainedEarningsAccumulatedDeficit_d2f5280a-09ef-4dc0-811d-1bf323d46fdc_terseLabel_en-US" xlink:label="lab_us-gaap_RetainedEarningsAccumulatedDeficit" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Accumulated loss</link:label>
    <link:label id="lab_us-gaap_RetainedEarningsAccumulatedDeficit_label_en-US" xlink:label="lab_us-gaap_RetainedEarningsAccumulatedDeficit" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Retained Earnings (Accumulated Deficit)</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_RetainedEarningsAccumulatedDeficit" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_RetainedEarningsAccumulatedDeficit"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_RetainedEarningsAccumulatedDeficit" xlink:to="lab_us-gaap_RetainedEarningsAccumulatedDeficit" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterTenYearsAmortizedCost_c0a61419-fb1a-4e77-962d-c7eff9f11473_terseLabel_en-US" xlink:label="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterTenYearsAmortizedCost" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Due after 10 years</link:label>
    <link:label id="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterTenYearsAmortizedCost_label_en-US" xlink:label="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterTenYearsAmortizedCost" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt Securities, Available-for-Sale, Amortized Cost, Maturity, Allocated and Single Maturity Date, after Year 10</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterTenYearsAmortizedCost" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterTenYearsAmortizedCost"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterTenYearsAmortizedCost" xlink:to="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterTenYearsAmortizedCost" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_USTreasuryAndGovernmentMember_21c52974-38de-410c-9ea9-54593d634e6c_terseLabel_en-US" xlink:label="lab_us-gaap_USTreasuryAndGovernmentMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">U.S. Treasury securities and agencies</link:label>
    <link:label id="lab_us-gaap_USTreasuryAndGovernmentMember_label_en-US" xlink:label="lab_us-gaap_USTreasuryAndGovernmentMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">US Treasury and Government [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_USTreasuryAndGovernmentMember" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_USTreasuryAndGovernmentMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_USTreasuryAndGovernmentMember" xlink:to="lab_us-gaap_USTreasuryAndGovernmentMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_StatementEquityComponentsAxis_d532f471-0b25-402d-ab59-09cc0d6d4727_terseLabel_en-US" xlink:label="lab_us-gaap_StatementEquityComponentsAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Equity Components [Axis]</link:label>
    <link:label id="lab_us-gaap_StatementEquityComponentsAxis_label_en-US" xlink:label="lab_us-gaap_StatementEquityComponentsAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Equity Components [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_StatementEquityComponentsAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_StatementEquityComponentsAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_StatementEquityComponentsAxis" xlink:to="lab_us-gaap_StatementEquityComponentsAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_ScenarioUnspecifiedDomain_52c0cc60-fe6e-42be-8020-93e54a2d16f2_terseLabel_en-US" xlink:label="lab_srt_ScenarioUnspecifiedDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Scenario [Domain]</link:label>
    <link:label id="lab_srt_ScenarioUnspecifiedDomain_label_en-US" xlink:label="lab_srt_ScenarioUnspecifiedDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Scenario [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_ScenarioUnspecifiedDomain" xlink:href="https://xbrl.fasb.org/srt/2022/elts/srt-2022.xsd#srt_ScenarioUnspecifiedDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_ScenarioUnspecifiedDomain" xlink:to="lab_srt_ScenarioUnspecifiedDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_StandardPoorsAAARatingMember_e8a05e46-b928-4572-929f-11d109bbe039_terseLabel_en-US" xlink:label="lab_srt_StandardPoorsAAARatingMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">AAA</link:label>
    <link:label id="lab_srt_StandardPoorsAAARatingMember_label_en-US" xlink:label="lab_srt_StandardPoorsAAARatingMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Standard &amp; Poor's, AAA Rating [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_StandardPoorsAAARatingMember" xlink:href="https://xbrl.fasb.org/srt/2022/elts/srt-2022.xsd#srt_StandardPoorsAAARatingMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_StandardPoorsAAARatingMember" xlink:to="lab_srt_StandardPoorsAAARatingMember" xlink:type="arc" order="1"/>
    <link:label id="lab_stpr_CO_0902c8e9-a433-4c2e-a440-c814b7562378_terseLabel_en-US" xlink:label="lab_stpr_CO" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Colorado</link:label>
    <link:label id="lab_stpr_CO_label_en-US" xlink:label="lab_stpr_CO" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">COLORADO</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_stpr_CO" xlink:href="https://xbrl.sec.gov/stpr/2022/stpr-2022.xsd#stpr_CO"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_stpr_CO" xlink:to="lab_stpr_CO" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPositionLessThan12Months_cfd3966e-de8c-4ff0-bcee-9b7c1e6ddae0_terseLabel_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPositionLessThan12Months" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Less than 12 months, fair value</link:label>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPositionLessThan12Months_label_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPositionLessThan12Months" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt Securities, Available-for-Sale, Continuous Unrealized Loss Position, Less than 12 Months</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPositionLessThan12Months" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPositionLessThan12Months"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPositionLessThan12Months" xlink:to="lab_us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPositionLessThan12Months" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_DocumentFiscalYearFocus_813c8eac-4d80-4a47-90df-6fa46c76fc81_terseLabel_en-US" xlink:label="lab_dei_DocumentFiscalYearFocus" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Document Fiscal Year Focus</link:label>
    <link:label id="lab_dei_DocumentFiscalYearFocus_label_en-US" xlink:label="lab_dei_DocumentFiscalYearFocus" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Document Fiscal Year Focus</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_DocumentFiscalYearFocus" xlink:href="https://xbrl.sec.gov/dei/2022/dei-2022.xsd#dei_DocumentFiscalYearFocus"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_DocumentFiscalYearFocus" xlink:to="lab_dei_DocumentFiscalYearFocus" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_NetCashProvidedByUsedInOperatingActivitiesAbstract_b456c343-3644-4d2b-b64f-a1e3d78cda1f_terseLabel_en-US" xlink:label="lab_us-gaap_NetCashProvidedByUsedInOperatingActivitiesAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Cash flows from operating activities:</link:label>
    <link:label id="lab_us-gaap_NetCashProvidedByUsedInOperatingActivitiesAbstract_label_en-US" xlink:label="lab_us-gaap_NetCashProvidedByUsedInOperatingActivitiesAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Net Cash Provided by (Used in) Operating Activities [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NetCashProvidedByUsedInOperatingActivitiesAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_NetCashProvidedByUsedInOperatingActivitiesAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_NetCashProvidedByUsedInOperatingActivitiesAbstract" xlink:to="lab_us-gaap_NetCashProvidedByUsedInOperatingActivitiesAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_StatementLineItems_66ea5d9b-af36-4eb1-8a11-75af719157be_terseLabel_en-US" xlink:label="lab_us-gaap_StatementLineItems" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Statement [Line Items]</link:label>
    <link:label id="lab_us-gaap_StatementLineItems_label_en-US" xlink:label="lab_us-gaap_StatementLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Statement [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_StatementLineItems" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_StatementLineItems"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_StatementLineItems" xlink:to="lab_us-gaap_StatementLineItems" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedNumber_d77fcb0e-4522-4584-bea0-19bf3ac3ea94_periodStartLabel_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedNumber" xlink:role="http://www.xbrl.org/2003/role/periodStartLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Beginning balance (in shares)</link:label>
    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedNumber_5499a33a-76a7-4559-97db-7e2e3198bb36_periodEndLabel_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedNumber" xlink:role="http://www.xbrl.org/2003/role/periodEndLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Ending balance (in shares)</link:label>
    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedNumber_label_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedNumber" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Share-Based Compensation Arrangement by Share-Based Payment Award, Equity Instruments Other than Options, Nonvested, Number</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedNumber" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedNumber"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedNumber" xlink:to="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedNumber" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_IncreaseDecreaseInLiabilityForClaimsAndClaimsAdjustmentExpenseReserve_3be74a34-e392-4c6f-8c45-267de54c495d_terseLabel_en-US" xlink:label="lab_us-gaap_IncreaseDecreaseInLiabilityForClaimsAndClaimsAdjustmentExpenseReserve" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Losses and loss adjustment expenses reserves</link:label>
    <link:label id="lab_us-gaap_IncreaseDecreaseInLiabilityForClaimsAndClaimsAdjustmentExpenseReserve_label_en-US" xlink:label="lab_us-gaap_IncreaseDecreaseInLiabilityForClaimsAndClaimsAdjustmentExpenseReserve" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Increase (Decrease) in Liability for Claims and Claims Adjustment Expense Reserve</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncreaseDecreaseInLiabilityForClaimsAndClaimsAdjustmentExpenseReserve" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_IncreaseDecreaseInLiabilityForClaimsAndClaimsAdjustmentExpenseReserve"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IncreaseDecreaseInLiabilityForClaimsAndClaimsAdjustmentExpenseReserve" xlink:to="lab_us-gaap_IncreaseDecreaseInLiabilityForClaimsAndClaimsAdjustmentExpenseReserve" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_VariableRateDomain_3fc02527-d1e9-4d94-82be-8905b4e12c8b_terseLabel_en-US" xlink:label="lab_us-gaap_VariableRateDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Variable Rate [Domain]</link:label>
    <link:label id="lab_us-gaap_VariableRateDomain_label_en-US" xlink:label="lab_us-gaap_VariableRateDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Variable Rate [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_VariableRateDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_VariableRateDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_VariableRateDomain" xlink:to="lab_us-gaap_VariableRateDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EffectsOfReinsuranceLineItems_527c2196-2dfc-43f1-9056-a8165d964f3f_terseLabel_en-US" xlink:label="lab_us-gaap_EffectsOfReinsuranceLineItems" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Effects of Reinsurance [Line Items]</link:label>
    <link:label id="lab_us-gaap_EffectsOfReinsuranceLineItems_label_en-US" xlink:label="lab_us-gaap_EffectsOfReinsuranceLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Effects of Reinsurance [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EffectsOfReinsuranceLineItems" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_EffectsOfReinsuranceLineItems"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EffectsOfReinsuranceLineItems" xlink:to="lab_us-gaap_EffectsOfReinsuranceLineItems" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FairValueByFairValueHierarchyLevelAxis_dc07536f-dff5-44c0-8d70-df9ea654415d_terseLabel_en-US" xlink:label="lab_us-gaap_FairValueByFairValueHierarchyLevelAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Fair Value Hierarchy and NAV [Axis]</link:label>
    <link:label id="lab_us-gaap_FairValueByFairValueHierarchyLevelAxis_label_en-US" xlink:label="lab_us-gaap_FairValueByFairValueHierarchyLevelAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Fair Value Hierarchy and NAV [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueByFairValueHierarchyLevelAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_FairValueByFairValueHierarchyLevelAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FairValueByFairValueHierarchyLevelAxis" xlink:to="lab_us-gaap_FairValueByFairValueHierarchyLevelAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AssumedPremiumsWritten_5c4f80f7-fd18-491c-ad05-433ee18ad747_terseLabel_en-US" xlink:label="lab_us-gaap_AssumedPremiumsWritten" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Assumed</link:label>
    <link:label id="lab_us-gaap_AssumedPremiumsWritten_label_en-US" xlink:label="lab_us-gaap_AssumedPremiumsWritten" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Assumed Premiums Written</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AssumedPremiumsWritten" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_AssumedPremiumsWritten"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AssumedPremiumsWritten" xlink:to="lab_us-gaap_AssumedPremiumsWritten" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_PremiumsWrittenNetConsolidatedAbstract_d56311ba-2413-441b-a247-d932874889b6_terseLabel_en-US" xlink:label="lab_us-gaap_PremiumsWrittenNetConsolidatedAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Premiums written:</link:label>
    <link:label id="lab_us-gaap_PremiumsWrittenNetConsolidatedAbstract_label_en-US" xlink:label="lab_us-gaap_PremiumsWrittenNetConsolidatedAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Premiums Written, Net [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PremiumsWrittenNetConsolidatedAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_PremiumsWrittenNetConsolidatedAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PremiumsWrittenNetConsolidatedAbstract" xlink:to="lab_us-gaap_PremiumsWrittenNetConsolidatedAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AvailableForSaleDebtSecuritiesAccumulatedGrossUnrealizedLossBeforeTax_07bb273b-8c41-4cfa-9e36-08e2e9b80cdd_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_AvailableForSaleDebtSecuritiesAccumulatedGrossUnrealizedLossBeforeTax" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Gross Unrealized Losses</link:label>
    <link:label id="lab_us-gaap_AvailableForSaleDebtSecuritiesAccumulatedGrossUnrealizedLossBeforeTax_label_en-US" xlink:label="lab_us-gaap_AvailableForSaleDebtSecuritiesAccumulatedGrossUnrealizedLossBeforeTax" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt Securities, Available-for-Sale, Accumulated Gross Unrealized Loss, before Tax</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AvailableForSaleDebtSecuritiesAccumulatedGrossUnrealizedLossBeforeTax" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_AvailableForSaleDebtSecuritiesAccumulatedGrossUnrealizedLossBeforeTax"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AvailableForSaleDebtSecuritiesAccumulatedGrossUnrealizedLossBeforeTax" xlink:to="lab_us-gaap_AvailableForSaleDebtSecuritiesAccumulatedGrossUnrealizedLossBeforeTax" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AccumulatedOtherComprehensiveIncomeMember_21fe658a-0d7d-4f1e-b4ec-0d5afa95489c_terseLabel_en-US" xlink:label="lab_us-gaap_AccumulatedOtherComprehensiveIncomeMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Accumulated Other Comprehensive Income (Loss)</link:label>
    <link:label id="lab_us-gaap_AccumulatedOtherComprehensiveIncomeMember_label_en-US" xlink:label="lab_us-gaap_AccumulatedOtherComprehensiveIncomeMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">AOCI Attributable to Parent [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AccumulatedOtherComprehensiveIncomeMember" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_AccumulatedOtherComprehensiveIncomeMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AccumulatedOtherComprehensiveIncomeMember" xlink:to="lab_us-gaap_AccumulatedOtherComprehensiveIncomeMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ComprehensiveIncomeNoteTextBlock_f800cc7b-27be-4c02-aeea-36a21a482156_terseLabel_en-US" xlink:label="lab_us-gaap_ComprehensiveIncomeNoteTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">OTHER COMPREHENSIVE LOSS AND ACCUMULATED OTHER COMPREHENSIVE (LOSS) INCOME</link:label>
    <link:label id="lab_us-gaap_ComprehensiveIncomeNoteTextBlock_label_en-US" xlink:label="lab_us-gaap_ComprehensiveIncomeNoteTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Comprehensive Income (Loss) Note [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ComprehensiveIncomeNoteTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ComprehensiveIncomeNoteTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ComprehensiveIncomeNoteTextBlock" xlink:to="lab_us-gaap_ComprehensiveIncomeNoteTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_root_OrganizationalRealignmentMember_d18a232d-7e61-4c7e-b5eb-a2ab7e2dc1f0_terseLabel_en-US" xlink:label="lab_root_OrganizationalRealignmentMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Organizational Realignment</link:label>
    <link:label id="lab_root_OrganizationalRealignmentMember_label_en-US" xlink:label="lab_root_OrganizationalRealignmentMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Organizational Realignment [Member]</link:label>
    <link:label id="lab_root_OrganizationalRealignmentMember_documentation_en-US" xlink:label="lab_root_OrganizationalRealignmentMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Organizational Realignment</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_root_OrganizationalRealignmentMember" xlink:href="root-20220930.xsd#root_OrganizationalRealignmentMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_root_OrganizationalRealignmentMember" xlink:to="lab_root_OrganizationalRealignmentMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_TypeOfRestructuringDomain_03d52542-9586-4fe1-8050-cbb07a9a59bf_terseLabel_en-US" xlink:label="lab_us-gaap_TypeOfRestructuringDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Type of Restructuring [Domain]</link:label>
    <link:label id="lab_us-gaap_TypeOfRestructuringDomain_label_en-US" xlink:label="lab_us-gaap_TypeOfRestructuringDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Type of Restructuring [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_TypeOfRestructuringDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_TypeOfRestructuringDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_TypeOfRestructuringDomain" xlink:to="lab_us-gaap_TypeOfRestructuringDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_DocumentTransitionReport_ba4f1199-d5d9-416c-9cb7-11e51f4c3578_terseLabel_en-US" xlink:label="lab_dei_DocumentTransitionReport" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Document Transition Report</link:label>
    <link:label id="lab_dei_DocumentTransitionReport_label_en-US" xlink:label="lab_dei_DocumentTransitionReport" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Document Transition Report</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_DocumentTransitionReport" xlink:href="https://xbrl.sec.gov/dei/2022/dei-2022.xsd#dei_DocumentTransitionReport"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_DocumentTransitionReport" xlink:to="lab_dei_DocumentTransitionReport" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_LocalPhoneNumber_60fdbac2-f7ef-4a89-aa5c-65d6095570e4_terseLabel_en-US" xlink:label="lab_dei_LocalPhoneNumber" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Local Phone Number</link:label>
    <link:label id="lab_dei_LocalPhoneNumber_label_en-US" xlink:label="lab_dei_LocalPhoneNumber" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Local Phone Number</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_LocalPhoneNumber" xlink:href="https://xbrl.sec.gov/dei/2022/dei-2022.xsd#dei_LocalPhoneNumber"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_LocalPhoneNumber" xlink:to="lab_dei_LocalPhoneNumber" xlink:type="arc" order="1"/>
    <link:label id="lab_root_LiabilityForClaimsAndClaimsAdjustmentExpenseMember_16254da3-8438-46b5-8686-2ad5131078a5_terseLabel_en-US" xlink:label="lab_root_LiabilityForClaimsAndClaimsAdjustmentExpenseMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Loss and loss adjustment expenses</link:label>
    <link:label id="lab_root_LiabilityForClaimsAndClaimsAdjustmentExpenseMember_label_en-US" xlink:label="lab_root_LiabilityForClaimsAndClaimsAdjustmentExpenseMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Liability For Claims And Claims Adjustment Expense [Member]</link:label>
    <link:label id="lab_root_LiabilityForClaimsAndClaimsAdjustmentExpenseMember_documentation_en-US" xlink:label="lab_root_LiabilityForClaimsAndClaimsAdjustmentExpenseMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Liability For Claims And Claims Adjustment Expense</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_root_LiabilityForClaimsAndClaimsAdjustmentExpenseMember" xlink:href="root-20220930.xsd#root_LiabilityForClaimsAndClaimsAdjustmentExpenseMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_root_LiabilityForClaimsAndClaimsAdjustmentExpenseMember" xlink:to="lab_root_LiabilityForClaimsAndClaimsAdjustmentExpenseMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ScheduleOfShareBasedCompensationStockOptionsActivityTableTextBlock_fbc62bc4-78c6-47d8-a2a0-f3a2c32bf005_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfShareBasedCompensationStockOptionsActivityTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Summary of Option Activity</link:label>
    <link:label id="lab_us-gaap_ScheduleOfShareBasedCompensationStockOptionsActivityTableTextBlock_label_en-US" xlink:label="lab_us-gaap_ScheduleOfShareBasedCompensationStockOptionsActivityTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Share-Based Payment Arrangement, Option, Activity [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfShareBasedCompensationStockOptionsActivityTableTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ScheduleOfShareBasedCompensationStockOptionsActivityTableTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ScheduleOfShareBasedCompensationStockOptionsActivityTableTextBlock" xlink:to="lab_us-gaap_ScheduleOfShareBasedCompensationStockOptionsActivityTableTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_OperatingIncomeLoss_b79d6cdc-32b3-4aa9-95eb-555640b530fc_totalLabel_en-US" xlink:label="lab_us-gaap_OperatingIncomeLoss" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Operating loss</link:label>
    <link:label id="lab_us-gaap_OperatingIncomeLoss_label_en-US" xlink:label="lab_us-gaap_OperatingIncomeLoss" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Operating Income (Loss)</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OperatingIncomeLoss" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_OperatingIncomeLoss"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_OperatingIncomeLoss" xlink:to="lab_us-gaap_OperatingIncomeLoss" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CommonStockSharesOutstanding_30a7e3b5-13df-4725-ba0d-63caff04925b_terseLabel_en-US" xlink:label="lab_us-gaap_CommonStockSharesOutstanding" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Common stock, shares outstanding (in shares)</link:label>
    <link:label id="lab_us-gaap_CommonStockSharesOutstanding_a893e183-9f0a-41a4-8864-22d13ffe0351_periodStartLabel_en-US" xlink:label="lab_us-gaap_CommonStockSharesOutstanding" xlink:role="http://www.xbrl.org/2003/role/periodStartLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Beginning balance (in shares)</link:label>
    <link:label id="lab_us-gaap_CommonStockSharesOutstanding_8a7e3f23-3558-4bf4-afe1-b0920b998b29_periodEndLabel_en-US" xlink:label="lab_us-gaap_CommonStockSharesOutstanding" xlink:role="http://www.xbrl.org/2003/role/periodEndLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Ending balance (in shares)</link:label>
    <link:label id="lab_us-gaap_CommonStockSharesOutstanding_label_en-US" xlink:label="lab_us-gaap_CommonStockSharesOutstanding" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Common Stock, Shares, Outstanding</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CommonStockSharesOutstanding" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_CommonStockSharesOutstanding"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CommonStockSharesOutstanding" xlink:to="lab_us-gaap_CommonStockSharesOutstanding" xlink:type="arc" order="1"/>
    <link:label id="lab_root_CreditRatingConcentrationRiskMember_e77a3a76-903b-41d6-854b-7ab4c1986d3e_terseLabel_en-US" xlink:label="lab_root_CreditRatingConcentrationRiskMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Credit rating</link:label>
    <link:label id="lab_root_CreditRatingConcentrationRiskMember_label_en-US" xlink:label="lab_root_CreditRatingConcentrationRiskMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Credit Rating Concentration Risk [Member]</link:label>
    <link:label id="lab_root_CreditRatingConcentrationRiskMember_documentation_en-US" xlink:label="lab_root_CreditRatingConcentrationRiskMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Credit Rating Concentration Risk</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_root_CreditRatingConcentrationRiskMember" xlink:href="root-20220930.xsd#root_CreditRatingConcentrationRiskMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_root_CreditRatingConcentrationRiskMember" xlink:to="lab_root_CreditRatingConcentrationRiskMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_TreasuryStockShares_c0305388-2cfa-4db9-af36-52544c2ba6ec_periodStartLabel_en-US" xlink:label="lab_us-gaap_TreasuryStockShares" xlink:role="http://www.xbrl.org/2003/role/periodStartLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Treasury stock, beginning balance (in shares)</link:label>
    <link:label id="lab_us-gaap_TreasuryStockShares_6e1aac99-0341-4317-8199-8247eebea98c_periodEndLabel_en-US" xlink:label="lab_us-gaap_TreasuryStockShares" xlink:role="http://www.xbrl.org/2003/role/periodEndLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Treasury stock, ending balance (in shares)</link:label>
    <link:label id="lab_us-gaap_TreasuryStockShares_label_en-US" xlink:label="lab_us-gaap_TreasuryStockShares" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Treasury Stock, Shares</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_TreasuryStockShares" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_TreasuryStockShares"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_TreasuryStockShares" xlink:to="lab_us-gaap_TreasuryStockShares" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AdjustmentsToReconcileNetIncomeLossToCashProvidedByUsedInOperatingActivitiesAbstract_6bcfe2e3-9888-4f0c-bccb-ab0157b3db06_terseLabel_en-US" xlink:label="lab_us-gaap_AdjustmentsToReconcileNetIncomeLossToCashProvidedByUsedInOperatingActivitiesAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Adjustments to reconcile net loss to net cash used in operating activities:</link:label>
    <link:label id="lab_us-gaap_AdjustmentsToReconcileNetIncomeLossToCashProvidedByUsedInOperatingActivitiesAbstract_label_en-US" xlink:label="lab_us-gaap_AdjustmentsToReconcileNetIncomeLossToCashProvidedByUsedInOperatingActivitiesAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Adjustments to Reconcile Net Income (Loss) to Cash Provided by (Used in) Operating Activities [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AdjustmentsToReconcileNetIncomeLossToCashProvidedByUsedInOperatingActivitiesAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_AdjustmentsToReconcileNetIncomeLossToCashProvidedByUsedInOperatingActivitiesAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AdjustmentsToReconcileNetIncomeLossToCashProvidedByUsedInOperatingActivitiesAbstract" xlink:to="lab_us-gaap_AdjustmentsToReconcileNetIncomeLossToCashProvidedByUsedInOperatingActivitiesAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_IncomeTaxExpenseBenefit_dbd24a9b-f858-4fe4-b091-7454f3c90f24_terseLabel_en-US" xlink:label="lab_us-gaap_IncomeTaxExpenseBenefit" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Income tax expense</link:label>
    <link:label id="lab_us-gaap_IncomeTaxExpenseBenefit_label_en-US" xlink:label="lab_us-gaap_IncomeTaxExpenseBenefit" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Income Tax Expense (Benefit)</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncomeTaxExpenseBenefit" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_IncomeTaxExpenseBenefit"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IncomeTaxExpenseBenefit" xlink:to="lab_us-gaap_IncomeTaxExpenseBenefit" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_SegmentGeographicalDomain_c1c662f1-4abb-4e3d-a676-6b1b5523bc66_terseLabel_en-US" xlink:label="lab_srt_SegmentGeographicalDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Geographical [Domain]</link:label>
    <link:label id="lab_srt_SegmentGeographicalDomain_label_en-US" xlink:label="lab_srt_SegmentGeographicalDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Geographical [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_SegmentGeographicalDomain" xlink:href="https://xbrl.fasb.org/srt/2022/elts/srt-2022.xsd#srt_SegmentGeographicalDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_SegmentGeographicalDomain" xlink:to="lab_srt_SegmentGeographicalDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_SharebasedCompensationArrangementBySharebasedPaymentAwardEquityInstrumentsOtherThanOptionsAggregateIntrinsicValueNonvested_f744cd3f-9930-49a8-b945-5ee18aedb826_periodStartLabel_en-US" xlink:label="lab_us-gaap_SharebasedCompensationArrangementBySharebasedPaymentAwardEquityInstrumentsOtherThanOptionsAggregateIntrinsicValueNonvested" xlink:role="http://www.xbrl.org/2003/role/periodStartLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Beginning balance</link:label>
    <link:label id="lab_us-gaap_SharebasedCompensationArrangementBySharebasedPaymentAwardEquityInstrumentsOtherThanOptionsAggregateIntrinsicValueNonvested_d3ed8bda-354b-41bd-b0f0-f760804f97fd_periodEndLabel_en-US" xlink:label="lab_us-gaap_SharebasedCompensationArrangementBySharebasedPaymentAwardEquityInstrumentsOtherThanOptionsAggregateIntrinsicValueNonvested" xlink:role="http://www.xbrl.org/2003/role/periodEndLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Ending balance</link:label>
    <link:label id="lab_us-gaap_SharebasedCompensationArrangementBySharebasedPaymentAwardEquityInstrumentsOtherThanOptionsAggregateIntrinsicValueNonvested_label_en-US" xlink:label="lab_us-gaap_SharebasedCompensationArrangementBySharebasedPaymentAwardEquityInstrumentsOtherThanOptionsAggregateIntrinsicValueNonvested" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Share-Based Compensation Arrangement by Share-Based Payment Award, Equity Instruments Other than Options, Aggregate Intrinsic Value, Nonvested</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SharebasedCompensationArrangementBySharebasedPaymentAwardEquityInstrumentsOtherThanOptionsAggregateIntrinsicValueNonvested" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_SharebasedCompensationArrangementBySharebasedPaymentAwardEquityInstrumentsOtherThanOptionsAggregateIntrinsicValueNonvested"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_SharebasedCompensationArrangementBySharebasedPaymentAwardEquityInstrumentsOtherThanOptionsAggregateIntrinsicValueNonvested" xlink:to="lab_us-gaap_SharebasedCompensationArrangementBySharebasedPaymentAwardEquityInstrumentsOtherThanOptionsAggregateIntrinsicValueNonvested" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_PreferredStockParOrStatedValuePerShare_e665f149-2e0d-4e2e-ab63-c94b651e4792_terseLabel_en-US" xlink:label="lab_us-gaap_PreferredStockParOrStatedValuePerShare" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Preferred stock, par value (in dollars per share)</link:label>
    <link:label id="lab_us-gaap_PreferredStockParOrStatedValuePerShare_label_en-US" xlink:label="lab_us-gaap_PreferredStockParOrStatedValuePerShare" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Preferred Stock, Par or Stated Value Per Share</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PreferredStockParOrStatedValuePerShare" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_PreferredStockParOrStatedValuePerShare"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PreferredStockParOrStatedValuePerShare" xlink:to="lab_us-gaap_PreferredStockParOrStatedValuePerShare" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_IncomeStatementAbstract_label_en-US" xlink:label="lab_us-gaap_IncomeStatementAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Income Statement [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncomeStatementAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_IncomeStatementAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IncomeStatementAbstract" xlink:to="lab_us-gaap_IncomeStatementAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardOptionsGrantsInPeriodGross_95b4d695-e6df-490c-9686-43a5082b610f_terseLabel_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardOptionsGrantsInPeriodGross" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Granted (in shares)</link:label>
    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardOptionsGrantsInPeriodGross_label_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardOptionsGrantsInPeriodGross" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Share-Based Compensation Arrangement by Share-Based Payment Award, Options, Grants in Period, Gross</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardOptionsGrantsInPeriodGross" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardOptionsGrantsInPeriodGross"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardOptionsGrantsInPeriodGross" xlink:to="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardOptionsGrantsInPeriodGross" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AdditionalPaidInCapitalMember_d6641dc6-a028-47ea-86e0-b2e07d221bbe_terseLabel_en-US" xlink:label="lab_us-gaap_AdditionalPaidInCapitalMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Additional Paid-in Capital</link:label>
    <link:label id="lab_us-gaap_AdditionalPaidInCapitalMember_label_en-US" xlink:label="lab_us-gaap_AdditionalPaidInCapitalMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Additional Paid-in Capital [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AdditionalPaidInCapitalMember" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_AdditionalPaidInCapitalMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AdditionalPaidInCapitalMember" xlink:to="lab_us-gaap_AdditionalPaidInCapitalMember" xlink:type="arc" order="1"/>
    <link:label id="lab_root_ClassOfWarrantOrRightNumberOfTranches_0158e338-2277-4d56-be7d-a3f75d42feb9_terseLabel_en-US" xlink:label="lab_root_ClassOfWarrantOrRightNumberOfTranches" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Number of tranches</link:label>
    <link:label id="lab_root_ClassOfWarrantOrRightNumberOfTranches_label_en-US" xlink:label="lab_root_ClassOfWarrantOrRightNumberOfTranches" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Class Of Warrant Or Right, Number Of Tranches</link:label>
    <link:label id="lab_root_ClassOfWarrantOrRightNumberOfTranches_documentation_en-US" xlink:label="lab_root_ClassOfWarrantOrRightNumberOfTranches" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Class Of Warrant Or Right, Number Of Tranches</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_root_ClassOfWarrantOrRightNumberOfTranches" xlink:href="root-20220930.xsd#root_ClassOfWarrantOrRightNumberOfTranches"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_root_ClassOfWarrantOrRightNumberOfTranches" xlink:to="lab_root_ClassOfWarrantOrRightNumberOfTranches" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_DocumentFiscalPeriodFocus_663d56cb-8acd-4b4c-8c20-13ad6076c3fb_terseLabel_en-US" xlink:label="lab_dei_DocumentFiscalPeriodFocus" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Document Fiscal Period Focus</link:label>
    <link:label id="lab_dei_DocumentFiscalPeriodFocus_label_en-US" xlink:label="lab_dei_DocumentFiscalPeriodFocus" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Document Fiscal Period Focus</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_DocumentFiscalPeriodFocus" xlink:href="https://xbrl.sec.gov/dei/2022/dei-2022.xsd#dei_DocumentFiscalPeriodFocus"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_DocumentFiscalPeriodFocus" xlink:to="lab_dei_DocumentFiscalPeriodFocus" xlink:type="arc" order="1"/>
    <link:label id="lab_root_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsCeded_0d4dc623-825d-4bc5-b9a4-6d14080d0096_negatedTerseLabel_en-US" xlink:label="lab_root_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsCeded" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Ceded</link:label>
    <link:label id="lab_root_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsCeded_label_en-US" xlink:label="lab_root_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsCeded" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Liability For Unpaid Claims And Claims Adjustment Expense, Incurred Claims, Ceded</link:label>
    <link:label id="lab_root_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsCeded_documentation_en-US" xlink:label="lab_root_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsCeded" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Liability For Unpaid Claims And Claims Adjustment Expense, Incurred Claims, Ceded</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_root_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsCeded" xlink:href="root-20220930.xsd#root_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsCeded"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_root_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsCeded" xlink:to="lab_root_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsCeded" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardOptionsExercisesInPeriodTotalIntrinsicValue_66113179-f143-44d0-9cf0-dcaad12d5326_terseLabel_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardOptionsExercisesInPeriodTotalIntrinsicValue" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Exercised, aggregate intrinsic value</link:label>
    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardOptionsExercisesInPeriodTotalIntrinsicValue_label_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardOptionsExercisesInPeriodTotalIntrinsicValue" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Share-Based Compensation Arrangement by Share-Based Payment Award, Options, Exercises in Period, Intrinsic Value</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardOptionsExercisesInPeriodTotalIntrinsicValue" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardOptionsExercisesInPeriodTotalIntrinsicValue"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardOptionsExercisesInPeriodTotalIntrinsicValue" xlink:to="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardOptionsExercisesInPeriodTotalIntrinsicValue" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_WeightedAverageNumberOfDilutedSharesOutstanding_2e4f0991-6141-4865-8b50-f7f1f8c6d02b_terseLabel_en-US" xlink:label="lab_us-gaap_WeightedAverageNumberOfDilutedSharesOutstanding" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Weighted-average common shares outstanding: diluted (both Class A and B) (in shares)</link:label>
    <link:label id="lab_us-gaap_WeightedAverageNumberOfDilutedSharesOutstanding_label_en-US" xlink:label="lab_us-gaap_WeightedAverageNumberOfDilutedSharesOutstanding" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Weighted Average Number of Shares Outstanding, Diluted</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_WeightedAverageNumberOfDilutedSharesOutstanding" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_WeightedAverageNumberOfDilutedSharesOutstanding"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_WeightedAverageNumberOfDilutedSharesOutstanding" xlink:to="lab_us-gaap_WeightedAverageNumberOfDilutedSharesOutstanding" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ScheduleOfAvailableForSaleSecuritiesLineItems_a5f78c19-557d-44c7-ba40-ceb71c67055a_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfAvailableForSaleSecuritiesLineItems" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt Securities, Available-for-sale [Line Items]</link:label>
    <link:label id="lab_us-gaap_ScheduleOfAvailableForSaleSecuritiesLineItems_label_en-US" xlink:label="lab_us-gaap_ScheduleOfAvailableForSaleSecuritiesLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt Securities, Available-for-Sale [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfAvailableForSaleSecuritiesLineItems" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ScheduleOfAvailableForSaleSecuritiesLineItems"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ScheduleOfAvailableForSaleSecuritiesLineItems" xlink:to="lab_us-gaap_ScheduleOfAvailableForSaleSecuritiesLineItems" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_Investments_982457ba-6540-4266-94d6-c50c0efa4ec7_totalLabel_en-US" xlink:label="lab_us-gaap_Investments" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Total investments</link:label>
    <link:label id="lab_us-gaap_Investments_label_en-US" xlink:label="lab_us-gaap_Investments" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Investments</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_Investments" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_Investments"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_Investments" xlink:to="lab_us-gaap_Investments" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CommonStockValue_2c509361-e3a7-4c1f-af48-3ba7d7bccdeb_verboseLabel_en-US" xlink:label="lab_us-gaap_CommonStockValue" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Common stock, value</link:label>
    <link:label id="lab_us-gaap_CommonStockValue_label_en-US" xlink:label="lab_us-gaap_CommonStockValue" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Common Stock, Value, Issued</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CommonStockValue" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_CommonStockValue"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CommonStockValue" xlink:to="lab_us-gaap_CommonStockValue" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CarryingReportedAmountFairValueDisclosureMember_6015b150-a866-456a-86be-cabf4792ddef_terseLabel_en-US" xlink:label="lab_us-gaap_CarryingReportedAmountFairValueDisclosureMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Carrying amount</link:label>
    <link:label id="lab_us-gaap_CarryingReportedAmountFairValueDisclosureMember_label_en-US" xlink:label="lab_us-gaap_CarryingReportedAmountFairValueDisclosureMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Reported Value Measurement [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CarryingReportedAmountFairValueDisclosureMember" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_CarryingReportedAmountFairValueDisclosureMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CarryingReportedAmountFairValueDisclosureMember" xlink:to="lab_us-gaap_CarryingReportedAmountFairValueDisclosureMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DebtInstrumentNameDomain_4acf0f73-8bbd-49ab-80c9-73d7cb122851_terseLabel_en-US" xlink:label="lab_us-gaap_DebtInstrumentNameDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt Instrument, Name [Domain]</link:label>
    <link:label id="lab_us-gaap_DebtInstrumentNameDomain_label_en-US" xlink:label="lab_us-gaap_DebtInstrumentNameDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt Instrument, Name [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtInstrumentNameDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_DebtInstrumentNameDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DebtInstrumentNameDomain" xlink:to="lab_us-gaap_DebtInstrumentNameDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsGrantsInPeriodWeightedAverageGrantDateFairValue_c064ca6e-4052-405d-afe1-f4576c4e3ad8_terseLabel_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsGrantsInPeriodWeightedAverageGrantDateFairValue" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Granted, weighted-average grant date fair value (in dollars per share)</link:label>
    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsGrantsInPeriodWeightedAverageGrantDateFairValue_label_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsGrantsInPeriodWeightedAverageGrantDateFairValue" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Share-Based Compensation Arrangement by Share-Based Payment Award, Equity Instruments Other than Options, Grants in Period, Weighted Average Grant Date Fair Value</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsGrantsInPeriodWeightedAverageGrantDateFairValue" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsGrantsInPeriodWeightedAverageGrantDateFairValue"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsGrantsInPeriodWeightedAverageGrantDateFairValue" xlink:to="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsGrantsInPeriodWeightedAverageGrantDateFairValue" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ScheduleOfAntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareTextBlock_9b8ae0bc-74f2-478a-a9ba-0f9c0717ea5f_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfAntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Schedule of Anti-Dilutive Securities</link:label>
    <link:label id="lab_us-gaap_ScheduleOfAntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareTextBlock_label_en-US" xlink:label="lab_us-gaap_ScheduleOfAntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Schedule of Antidilutive Securities Excluded from Computation of Earnings Per Share [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfAntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ScheduleOfAntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ScheduleOfAntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareTextBlock" xlink:to="lab_us-gaap_ScheduleOfAntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_RealizedInvestmentGainsLosses_4ffb56d0-6b02-49e1-a1f8-2548b12f0798_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_RealizedInvestmentGainsLosses" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Net realized gains on investments</link:label>
    <link:label id="lab_us-gaap_RealizedInvestmentGainsLosses_label_en-US" xlink:label="lab_us-gaap_RealizedInvestmentGainsLosses" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Realized Investment Gains (Losses)</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_RealizedInvestmentGainsLosses" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_RealizedInvestmentGainsLosses"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_RealizedInvestmentGainsLosses" xlink:to="lab_us-gaap_RealizedInvestmentGainsLosses" xlink:type="arc" order="1"/>
    <link:label id="lab_root_DebtInstrumentCovenantComplianceInsurancePoliciesIssued_454e0f7b-60de-402f-9a27-91a228a95379_terseLabel_en-US" xlink:label="lab_root_DebtInstrumentCovenantComplianceInsurancePoliciesIssued" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt instrument, issued shares insurance policies (in shares)</link:label>
    <link:label id="lab_root_DebtInstrumentCovenantComplianceInsurancePoliciesIssued_label_en-US" xlink:label="lab_root_DebtInstrumentCovenantComplianceInsurancePoliciesIssued" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt Instrument, Covenant Compliance, Insurance Policies Issued</link:label>
    <link:label id="lab_root_DebtInstrumentCovenantComplianceInsurancePoliciesIssued_documentation_en-US" xlink:label="lab_root_DebtInstrumentCovenantComplianceInsurancePoliciesIssued" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt Instrument, Covenant Compliance, Insurance Policies Issued</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_root_DebtInstrumentCovenantComplianceInsurancePoliciesIssued" xlink:href="root-20220930.xsd#root_DebtInstrumentCovenantComplianceInsurancePoliciesIssued"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_root_DebtInstrumentCovenantComplianceInsurancePoliciesIssued" xlink:to="lab_root_DebtInstrumentCovenantComplianceInsurancePoliciesIssued" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_OtherIncome_0fdae1f6-6ebb-4574-a5e9-f5a9b71bc6ed_terseLabel_en-US" xlink:label="lab_us-gaap_OtherIncome" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Fee and other income</link:label>
    <link:label id="lab_us-gaap_OtherIncome_label_en-US" xlink:label="lab_us-gaap_OtherIncome" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Other Income</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OtherIncome" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_OtherIncome"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_OtherIncome" xlink:to="lab_us-gaap_OtherIncome" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_PreferredStockSharesAuthorized_09e7a2a6-d9d3-410b-b8f9-b4034dce5c28_terseLabel_en-US" xlink:label="lab_us-gaap_PreferredStockSharesAuthorized" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Preferred stock, shares authorized (in shares)</link:label>
    <link:label id="lab_us-gaap_PreferredStockSharesAuthorized_label_en-US" xlink:label="lab_us-gaap_PreferredStockSharesAuthorized" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Preferred Stock, Shares Authorized</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PreferredStockSharesAuthorized" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_PreferredStockSharesAuthorized"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PreferredStockSharesAuthorized" xlink:to="lab_us-gaap_PreferredStockSharesAuthorized" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalents_05e1204b-468a-403e-92d8-a1f110a4188a_periodStartLabel_en-US" xlink:label="lab_us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalents" xlink:role="http://www.xbrl.org/2003/role/periodStartLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Cash, cash equivalents and restricted cash at beginning of period</link:label>
    <link:label id="lab_us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalents_f81118f3-4a38-4605-a295-9beda3226216_periodEndLabel_en-US" xlink:label="lab_us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalents" xlink:role="http://www.xbrl.org/2003/role/periodEndLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Cash, cash equivalents and restricted cash at end of period</link:label>
    <link:label id="lab_us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalents_72f9d6fd-b8bd-4d48-a21a-aabff6c57280_totalLabel_en-US" xlink:label="lab_us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalents" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Total cash, cash equivalents and restricted cash shown in the condensed consolidated statements of cash flows</link:label>
    <link:label id="lab_us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalents_label_en-US" xlink:label="lab_us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalents" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Cash, Cash Equivalents, Restricted Cash, and Restricted Cash Equivalents</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalents" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalents"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalents" xlink:to="lab_us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalents" xlink:type="arc" order="1"/>
    <link:label id="lab_root_DebtInstrumentCovenantComplianceMinimumCashAndCashEquivalents_b5d42735-9ec9-449b-99b6-07df33d7a801_terseLabel_en-US" xlink:label="lab_root_DebtInstrumentCovenantComplianceMinimumCashAndCashEquivalents" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Insurance subsidiaries amount</link:label>
    <link:label id="lab_root_DebtInstrumentCovenantComplianceMinimumCashAndCashEquivalents_label_en-US" xlink:label="lab_root_DebtInstrumentCovenantComplianceMinimumCashAndCashEquivalents" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt Instrument, Covenant Compliance, Minimum Cash And Cash Equivalents</link:label>
    <link:label id="lab_root_DebtInstrumentCovenantComplianceMinimumCashAndCashEquivalents_documentation_en-US" xlink:label="lab_root_DebtInstrumentCovenantComplianceMinimumCashAndCashEquivalents" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt Instrument, Covenant Compliance, Minimum Cash And Cash Equivalents</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_root_DebtInstrumentCovenantComplianceMinimumCashAndCashEquivalents" xlink:href="root-20220930.xsd#root_DebtInstrumentCovenantComplianceMinimumCashAndCashEquivalents"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_root_DebtInstrumentCovenantComplianceMinimumCashAndCashEquivalents" xlink:to="lab_root_DebtInstrumentCovenantComplianceMinimumCashAndCashEquivalents" xlink:type="arc" order="1"/>
    <link:label id="lab_root_DebtSecuritiesAvailableForSaleMember_eaa3910e-5957-431e-b671-57a928dff6f8_terseLabel_en-US" xlink:label="lab_root_DebtSecuritiesAvailableForSaleMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">AFS securities</link:label>
    <link:label id="lab_root_DebtSecuritiesAvailableForSaleMember_label_en-US" xlink:label="lab_root_DebtSecuritiesAvailableForSaleMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt Securities, Available For Sale [Member]</link:label>
    <link:label id="lab_root_DebtSecuritiesAvailableForSaleMember_documentation_en-US" xlink:label="lab_root_DebtSecuritiesAvailableForSaleMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt Securities, Available For Sale</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_root_DebtSecuritiesAvailableForSaleMember" xlink:href="root-20220930.xsd#root_DebtSecuritiesAvailableForSaleMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_root_DebtSecuritiesAvailableForSaleMember" xlink:to="lab_root_DebtSecuritiesAvailableForSaleMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EffectsOfReinsuranceTableTextBlock_a1abcfc1-28a3-4fe5-aa60-72e528d99bf0_verboseLabel_en-US" xlink:label="lab_us-gaap_EffectsOfReinsuranceTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Schedule of Comprehensive Loss For Reinsurance</link:label>
    <link:label id="lab_us-gaap_EffectsOfReinsuranceTableTextBlock_64bc5ee7-790e-4505-bde2-5a0f69d48608_terseLabel_en-US" xlink:label="lab_us-gaap_EffectsOfReinsuranceTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Schedule of Direct and Assumed Written Premiums</link:label>
    <link:label id="lab_us-gaap_EffectsOfReinsuranceTableTextBlock_label_en-US" xlink:label="lab_us-gaap_EffectsOfReinsuranceTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Effects of Reinsurance [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EffectsOfReinsuranceTableTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_EffectsOfReinsuranceTableTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EffectsOfReinsuranceTableTextBlock" xlink:to="lab_us-gaap_EffectsOfReinsuranceTableTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CommitmentsAndContingenciesDisclosureTextBlock_d4c89aa4-ef87-4ed1-9220-fc18e0a8921a_terseLabel_en-US" xlink:label="lab_us-gaap_CommitmentsAndContingenciesDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">COMMITMENTS AND CONTINGENCIES</link:label>
    <link:label id="lab_us-gaap_CommitmentsAndContingenciesDisclosureTextBlock_label_en-US" xlink:label="lab_us-gaap_CommitmentsAndContingenciesDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Commitments and Contingencies Disclosure [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CommitmentsAndContingenciesDisclosureTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_CommitmentsAndContingenciesDisclosureTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CommitmentsAndContingenciesDisclosureTextBlock" xlink:to="lab_us-gaap_CommitmentsAndContingenciesDisclosureTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AdjustmentsToAdditionalPaidInCapitalWarrantIssued_e6c72a99-a7b9-4464-bb43-07d8be15f5a9_terseLabel_en-US" xlink:label="lab_us-gaap_AdjustmentsToAdditionalPaidInCapitalWarrantIssued" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Term Loan warrants issued</link:label>
    <link:label id="lab_us-gaap_AdjustmentsToAdditionalPaidInCapitalWarrantIssued_label_en-US" xlink:label="lab_us-gaap_AdjustmentsToAdditionalPaidInCapitalWarrantIssued" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Adjustments to Additional Paid in Capital, Warrant Issued</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AdjustmentsToAdditionalPaidInCapitalWarrantIssued" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_AdjustmentsToAdditionalPaidInCapitalWarrantIssued"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AdjustmentsToAdditionalPaidInCapitalWarrantIssued" xlink:to="lab_us-gaap_AdjustmentsToAdditionalPaidInCapitalWarrantIssued" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ProceedsFromStockOptionsExercised_eaa71ac6-bacf-4b01-a6ef-bec339baf28e_terseLabel_en-US" xlink:label="lab_us-gaap_ProceedsFromStockOptionsExercised" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Proceeds from exercise of stock options and restricted stock units, net of tax proceeds/(withholding)</link:label>
    <link:label id="lab_us-gaap_ProceedsFromStockOptionsExercised_label_en-US" xlink:label="lab_us-gaap_ProceedsFromStockOptionsExercised" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Proceeds from Stock Options Exercised</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ProceedsFromStockOptionsExercised" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ProceedsFromStockOptionsExercised"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ProceedsFromStockOptionsExercised" xlink:to="lab_us-gaap_ProceedsFromStockOptionsExercised" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CommonStockSharesIssued_515a5fef-dbdd-439f-b15e-6b3bd4554649_terseLabel_en-US" xlink:label="lab_us-gaap_CommonStockSharesIssued" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Common stock, shares issued (in shares)</link:label>
    <link:label id="lab_us-gaap_CommonStockSharesIssued_label_en-US" xlink:label="lab_us-gaap_CommonStockSharesIssued" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Common Stock, Shares, Issued</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CommonStockSharesIssued" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_CommonStockSharesIssued"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CommonStockSharesIssued" xlink:to="lab_us-gaap_CommonStockSharesIssued" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_IncomeStatementLocationDomain_7c2f1490-c908-4bd8-88b3-ef32c0ee98ff_terseLabel_en-US" xlink:label="lab_us-gaap_IncomeStatementLocationDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Income Statement Location [Domain]</link:label>
    <link:label id="lab_us-gaap_IncomeStatementLocationDomain_label_en-US" xlink:label="lab_us-gaap_IncomeStatementLocationDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Income Statement Location [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncomeStatementLocationDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_IncomeStatementLocationDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IncomeStatementLocationDomain" xlink:to="lab_us-gaap_IncomeStatementLocationDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleUnrealizedLossPosition_af5d3674-7b31-467e-b902-dca2e6f742ef_totalLabel_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleUnrealizedLossPosition" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Total, fair value</link:label>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleUnrealizedLossPosition_label_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleUnrealizedLossPosition" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt Securities, Available-for-Sale, Unrealized Loss Position</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtSecuritiesAvailableForSaleUnrealizedLossPosition" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_DebtSecuritiesAvailableForSaleUnrealizedLossPosition"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DebtSecuritiesAvailableForSaleUnrealizedLossPosition" xlink:to="lab_us-gaap_DebtSecuritiesAvailableForSaleUnrealizedLossPosition" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_AmendmentFlag_f46c018e-4188-46c7-804b-3b9c5662a108_terseLabel_en-US" xlink:label="lab_dei_AmendmentFlag" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Amendment Flag</link:label>
    <link:label id="lab_dei_AmendmentFlag_label_en-US" xlink:label="lab_dei_AmendmentFlag" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Amendment Flag</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_AmendmentFlag" xlink:href="https://xbrl.sec.gov/dei/2022/dei-2022.xsd#dei_AmendmentFlag"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_AmendmentFlag" xlink:to="lab_dei_AmendmentFlag" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_NetCashProvidedByUsedInInvestingActivities_f7da8849-3de2-41f4-acba-d38cadf84b32_totalLabel_en-US" xlink:label="lab_us-gaap_NetCashProvidedByUsedInInvestingActivities" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Net cash (used in) provided by investing activities</link:label>
    <link:label id="lab_us-gaap_NetCashProvidedByUsedInInvestingActivities_label_en-US" xlink:label="lab_us-gaap_NetCashProvidedByUsedInInvestingActivities" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Net Cash Provided by (Used in) Investing Activities</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NetCashProvidedByUsedInInvestingActivities" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_NetCashProvidedByUsedInInvestingActivities"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_NetCashProvidedByUsedInInvestingActivities" xlink:to="lab_us-gaap_NetCashProvidedByUsedInInvestingActivities" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DebtInstrumentFaceAmount_53ce0c18-5059-458a-86c5-330f3d6d8707_terseLabel_en-US" xlink:label="lab_us-gaap_DebtInstrumentFaceAmount" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt amount</link:label>
    <link:label id="lab_us-gaap_DebtInstrumentFaceAmount_label_en-US" xlink:label="lab_us-gaap_DebtInstrumentFaceAmount" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt Instrument, Face Amount</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtInstrumentFaceAmount" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_DebtInstrumentFaceAmount"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DebtInstrumentFaceAmount" xlink:to="lab_us-gaap_DebtInstrumentFaceAmount" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_InvestmentTypeAxis_1b93085b-7fa9-4b57-826e-ba324a919c23_terseLabel_en-US" xlink:label="lab_us-gaap_InvestmentTypeAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Investment Type [Axis]</link:label>
    <link:label id="lab_us-gaap_InvestmentTypeAxis_label_en-US" xlink:label="lab_us-gaap_InvestmentTypeAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Investment Type [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_InvestmentTypeAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_InvestmentTypeAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_InvestmentTypeAxis" xlink:to="lab_us-gaap_InvestmentTypeAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ComprehensiveIncomeNetOfTax_9ebfd21f-bd42-4129-950a-9eb2dbed2214_totalLabel_en-US" xlink:label="lab_us-gaap_ComprehensiveIncomeNetOfTax" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Comprehensive loss</link:label>
    <link:label id="lab_us-gaap_ComprehensiveIncomeNetOfTax_label_en-US" xlink:label="lab_us-gaap_ComprehensiveIncomeNetOfTax" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Comprehensive Income (Loss), Net of Tax, Attributable to Parent</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ComprehensiveIncomeNetOfTax" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ComprehensiveIncomeNetOfTax"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ComprehensiveIncomeNetOfTax" xlink:to="lab_us-gaap_ComprehensiveIncomeNetOfTax" xlink:type="arc" order="1"/>
    <link:label id="lab_root_OtherInsuranceExpenseIncome_5d11d18a-61dc-4795-a680-d3f56605aa2e_terseLabel_en-US" xlink:label="lab_root_OtherInsuranceExpenseIncome" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Other insurance expense (benefit)</link:label>
    <link:label id="lab_root_OtherInsuranceExpenseIncome_label_en-US" xlink:label="lab_root_OtherInsuranceExpenseIncome" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Other Insurance Expense (Income)</link:label>
    <link:label id="lab_root_OtherInsuranceExpenseIncome_documentation_en-US" xlink:label="lab_root_OtherInsuranceExpenseIncome" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Other Insurance Expense (Income)</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_root_OtherInsuranceExpenseIncome" xlink:href="root-20220930.xsd#root_OtherInsuranceExpenseIncome"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_root_OtherInsuranceExpenseIncome" xlink:to="lab_root_OtherInsuranceExpenseIncome" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AvailableForSaleDebtSecuritiesAccumulatedGrossUnrealizedGainBeforeTax_b961c55d-5dc3-4710-8770-228b2f9a6bb3_terseLabel_en-US" xlink:label="lab_us-gaap_AvailableForSaleDebtSecuritiesAccumulatedGrossUnrealizedGainBeforeTax" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Gross Unrealized Gains</link:label>
    <link:label id="lab_us-gaap_AvailableForSaleDebtSecuritiesAccumulatedGrossUnrealizedGainBeforeTax_label_en-US" xlink:label="lab_us-gaap_AvailableForSaleDebtSecuritiesAccumulatedGrossUnrealizedGainBeforeTax" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt Securities, Available-for-Sale, Accumulated Gross Unrealized Gain, before Tax</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AvailableForSaleDebtSecuritiesAccumulatedGrossUnrealizedGainBeforeTax" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_AvailableForSaleDebtSecuritiesAccumulatedGrossUnrealizedGainBeforeTax"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AvailableForSaleDebtSecuritiesAccumulatedGrossUnrealizedGainBeforeTax" xlink:to="lab_us-gaap_AvailableForSaleDebtSecuritiesAccumulatedGrossUnrealizedGainBeforeTax" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_EntityCurrentReportingStatus_47626bfd-cee1-4a9e-bf40-4ac9fdd42dff_terseLabel_en-US" xlink:label="lab_dei_EntityCurrentReportingStatus" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Entity Current Reporting Status</link:label>
    <link:label id="lab_dei_EntityCurrentReportingStatus_label_en-US" xlink:label="lab_dei_EntityCurrentReportingStatus" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Entity Current Reporting Status</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_EntityCurrentReportingStatus" xlink:href="https://xbrl.sec.gov/dei/2022/dei-2022.xsd#dei_EntityCurrentReportingStatus"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_EntityCurrentReportingStatus" xlink:to="lab_dei_EntityCurrentReportingStatus" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_PaymentsForRestructuring_45bd9037-3745-49af-a1ee-dd4ac7b7b34a_terseLabel_en-US" xlink:label="lab_us-gaap_PaymentsForRestructuring" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Cash expenditures</link:label>
    <link:label id="lab_us-gaap_PaymentsForRestructuring_label_en-US" xlink:label="lab_us-gaap_PaymentsForRestructuring" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Payments for Restructuring</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PaymentsForRestructuring" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_PaymentsForRestructuring"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PaymentsForRestructuring" xlink:to="lab_us-gaap_PaymentsForRestructuring" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidAbstract_48e7941d-6467-4f8b-8069-d1a755672671_terseLabel_en-US" xlink:label="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Net paid loss and LAE related to:</link:label>
    <link:label id="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidAbstract_label_en-US" xlink:label="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Liability for Unpaid Claims and Claims Adjustment Expense, Claims Paid [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidAbstract" xlink:to="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EmployeeSeveranceMember_e9ffc19c-137b-4bcd-96d7-0150889b0b01_terseLabel_en-US" xlink:label="lab_us-gaap_EmployeeSeveranceMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Severance, benefits, and related costs</link:label>
    <link:label id="lab_us-gaap_EmployeeSeveranceMember_label_en-US" xlink:label="lab_us-gaap_EmployeeSeveranceMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Employee Severance [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EmployeeSeveranceMember" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_EmployeeSeveranceMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EmployeeSeveranceMember" xlink:to="lab_us-gaap_EmployeeSeveranceMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EffectiveIncomeTaxRateReconciliationAtFederalStatutoryIncomeTaxRate_e117cd5f-18df-4e99-88ea-d6900a55e62d_terseLabel_en-US" xlink:label="lab_us-gaap_EffectiveIncomeTaxRateReconciliationAtFederalStatutoryIncomeTaxRate" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Federal income tax rate (in percent)</link:label>
    <link:label id="lab_us-gaap_EffectiveIncomeTaxRateReconciliationAtFederalStatutoryIncomeTaxRate_label_en-US" xlink:label="lab_us-gaap_EffectiveIncomeTaxRateReconciliationAtFederalStatutoryIncomeTaxRate" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Effective Income Tax Rate Reconciliation, at Federal Statutory Income Tax Rate, Percent</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EffectiveIncomeTaxRateReconciliationAtFederalStatutoryIncomeTaxRate" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_EffectiveIncomeTaxRateReconciliationAtFederalStatutoryIncomeTaxRate"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EffectiveIncomeTaxRateReconciliationAtFederalStatutoryIncomeTaxRate" xlink:to="lab_us-gaap_EffectiveIncomeTaxRateReconciliationAtFederalStatutoryIncomeTaxRate" xlink:type="arc" order="1"/>
    <link:label id="lab_root_ShareBasedCompensationAwardTrancheFiveMember_333e8cdd-0021-4e71-a40c-7b05737e0c3d_terseLabel_en-US" xlink:label="lab_root_ShareBasedCompensationAwardTrancheFiveMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Tranche 5</link:label>
    <link:label id="lab_root_ShareBasedCompensationAwardTrancheFiveMember_label_en-US" xlink:label="lab_root_ShareBasedCompensationAwardTrancheFiveMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Share Based Compensation Award Tranche Five [Member]</link:label>
    <link:label id="lab_root_ShareBasedCompensationAwardTrancheFiveMember_documentation_en-US" xlink:label="lab_root_ShareBasedCompensationAwardTrancheFiveMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Share Based Compensation Award Tranche Five</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_root_ShareBasedCompensationAwardTrancheFiveMember" xlink:href="root-20220930.xsd#root_ShareBasedCompensationAwardTrancheFiveMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_root_ShareBasedCompensationAwardTrancheFiveMember" xlink:to="lab_root_ShareBasedCompensationAwardTrancheFiveMember" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_CounterpartyNameAxis_a8485a66-e033-4935-85e1-1aa382d42bae_terseLabel_en-US" xlink:label="lab_srt_CounterpartyNameAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Counterparty Name [Axis]</link:label>
    <link:label id="lab_srt_CounterpartyNameAxis_label_en-US" xlink:label="lab_srt_CounterpartyNameAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Counterparty Name [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_CounterpartyNameAxis" xlink:href="https://xbrl.fasb.org/srt/2022/elts/srt-2022.xsd#srt_CounterpartyNameAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_CounterpartyNameAxis" xlink:to="lab_srt_CounterpartyNameAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AccumulatedOtherComprehensiveIncomeLossTable_678c74d2-02c8-4a88-8de4-d56313269441_terseLabel_en-US" xlink:label="lab_us-gaap_AccumulatedOtherComprehensiveIncomeLossTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Accumulated Other Comprehensive Income (Loss) [Table]</link:label>
    <link:label id="lab_us-gaap_AccumulatedOtherComprehensiveIncomeLossTable_label_en-US" xlink:label="lab_us-gaap_AccumulatedOtherComprehensiveIncomeLossTable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Accumulated Other Comprehensive Income (Loss) [Table]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AccumulatedOtherComprehensiveIncomeLossTable" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_AccumulatedOtherComprehensiveIncomeLossTable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AccumulatedOtherComprehensiveIncomeLossTable" xlink:to="lab_us-gaap_AccumulatedOtherComprehensiveIncomeLossTable" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardOptionsOutstandingNumber_08c98c19-2384-43cc-9c8d-f5c1a11de4f5_periodStartLabel_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardOptionsOutstandingNumber" xlink:role="http://www.xbrl.org/2003/role/periodStartLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Outstanding, beginning balance (in shares)</link:label>
    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardOptionsOutstandingNumber_c1fdaeba-987f-4d10-83a7-1c4461d16127_periodEndLabel_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardOptionsOutstandingNumber" xlink:role="http://www.xbrl.org/2003/role/periodEndLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Outstanding, ending balance (in shares)</link:label>
    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardOptionsOutstandingNumber_label_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardOptionsOutstandingNumber" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Share-Based Compensation Arrangement by Share-Based Payment Award, Options, Outstanding, Number</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardOptionsOutstandingNumber" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardOptionsOutstandingNumber"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardOptionsOutstandingNumber" xlink:to="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardOptionsOutstandingNumber" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DebtInstrumentUnamortizedDiscountPremiumAndDebtIssuanceCostsNet_e682a10d-211a-412c-b50e-90613c7e27f5_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_DebtInstrumentUnamortizedDiscountPremiumAndDebtIssuanceCostsNet" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Unamortized discount, debt issuance costs and warrants</link:label>
    <link:label id="lab_us-gaap_DebtInstrumentUnamortizedDiscountPremiumAndDebtIssuanceCostsNet_label_en-US" xlink:label="lab_us-gaap_DebtInstrumentUnamortizedDiscountPremiumAndDebtIssuanceCostsNet" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt Instrument, Unamortized Discount (Premium) and Debt Issuance Costs, Net</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtInstrumentUnamortizedDiscountPremiumAndDebtIssuanceCostsNet" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_DebtInstrumentUnamortizedDiscountPremiumAndDebtIssuanceCostsNet"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DebtInstrumentUnamortizedDiscountPremiumAndDebtIssuanceCostsNet" xlink:to="lab_us-gaap_DebtInstrumentUnamortizedDiscountPremiumAndDebtIssuanceCostsNet" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ScheduleOfStockByClassTable_e12eddae-cb45-4c2f-9c1d-b60508d020ac_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfStockByClassTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Schedule of Stock by Class [Table]</link:label>
    <link:label id="lab_us-gaap_ScheduleOfStockByClassTable_label_en-US" xlink:label="lab_us-gaap_ScheduleOfStockByClassTable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Schedule of Stock by Class [Table]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfStockByClassTable" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ScheduleOfStockByClassTable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ScheduleOfStockByClassTable" xlink:to="lab_us-gaap_ScheduleOfStockByClassTable" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_EntityIncorporationStateCountryCode_ac97e7b2-64e3-4acc-99d3-9cdac73c92f6_terseLabel_en-US" xlink:label="lab_dei_EntityIncorporationStateCountryCode" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Entity Incorporation, State or Country Code</link:label>
    <link:label id="lab_dei_EntityIncorporationStateCountryCode_label_en-US" xlink:label="lab_dei_EntityIncorporationStateCountryCode" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Entity Incorporation, State or Country Code</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_EntityIncorporationStateCountryCode" xlink:href="https://xbrl.sec.gov/dei/2022/dei-2022.xsd#dei_EntityIncorporationStateCountryCode"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_EntityIncorporationStateCountryCode" xlink:to="lab_dei_EntityIncorporationStateCountryCode" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_BasisOfAccountingPolicyPolicyTextBlock_20104b84-04dc-4fc1-8cc6-0b9d64a3ade8_terseLabel_en-US" xlink:label="lab_us-gaap_BasisOfAccountingPolicyPolicyTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Basis of Presentation</link:label>
    <link:label id="lab_us-gaap_BasisOfAccountingPolicyPolicyTextBlock_label_en-US" xlink:label="lab_us-gaap_BasisOfAccountingPolicyPolicyTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Basis of Accounting, Policy [Policy Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_BasisOfAccountingPolicyPolicyTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_BasisOfAccountingPolicyPolicyTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_BasisOfAccountingPolicyPolicyTextBlock" xlink:to="lab_us-gaap_BasisOfAccountingPolicyPolicyTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LiabilitiesAbstract_dc4f333f-119d-46d6-bfc2-b7328976f8dc_terseLabel_en-US" xlink:label="lab_us-gaap_LiabilitiesAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Liabilities:</link:label>
    <link:label id="lab_us-gaap_LiabilitiesAbstract_label_en-US" xlink:label="lab_us-gaap_LiabilitiesAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Liabilities [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LiabilitiesAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_LiabilitiesAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LiabilitiesAbstract" xlink:to="lab_us-gaap_LiabilitiesAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DepreciationAmortizationAndAccretionNet_0d3de5aa-f783-4831-9870-e6830c0d2f9a_terseLabel_en-US" xlink:label="lab_us-gaap_DepreciationAmortizationAndAccretionNet" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Depreciation and amortization</link:label>
    <link:label id="lab_us-gaap_DepreciationAmortizationAndAccretionNet_label_en-US" xlink:label="lab_us-gaap_DepreciationAmortizationAndAccretionNet" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Depreciation, Amortization and Accretion, Net</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DepreciationAmortizationAndAccretionNet" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_DepreciationAmortizationAndAccretionNet"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DepreciationAmortizationAndAccretionNet" xlink:to="lab_us-gaap_DepreciationAmortizationAndAccretionNet" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_RepaymentsOfLongTermDebt_9fa24970-0e3e-4611-b28c-495a8568b93d_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_RepaymentsOfLongTermDebt" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Repayments of long-term debt</link:label>
    <link:label id="lab_us-gaap_RepaymentsOfLongTermDebt_label_en-US" xlink:label="lab_us-gaap_RepaymentsOfLongTermDebt" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Repayments of Long-Term Debt</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_RepaymentsOfLongTermDebt" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_RepaymentsOfLongTermDebt"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_RepaymentsOfLongTermDebt" xlink:to="lab_us-gaap_RepaymentsOfLongTermDebt" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_SellingAndMarketingExpenseMember_225062e2-aa22-4392-93bc-1722d9a173b1_terseLabel_en-US" xlink:label="lab_us-gaap_SellingAndMarketingExpenseMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Sales and marketing</link:label>
    <link:label id="lab_us-gaap_SellingAndMarketingExpenseMember_label_en-US" xlink:label="lab_us-gaap_SellingAndMarketingExpenseMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Selling and Marketing Expense [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SellingAndMarketingExpenseMember" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_SellingAndMarketingExpenseMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_SellingAndMarketingExpenseMember" xlink:to="lab_us-gaap_SellingAndMarketingExpenseMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EmployeeStockOptionMember_ed2136b4-b1b5-4320-b5ea-ec2ade7c5689_terseLabel_en-US" xlink:label="lab_us-gaap_EmployeeStockOptionMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Stock option expense</link:label>
    <link:label id="lab_us-gaap_EmployeeStockOptionMember_f23db34a-3421-4c1f-88fe-9c197f885302_verboseLabel_en-US" xlink:label="lab_us-gaap_EmployeeStockOptionMember" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Options to purchase common stock</link:label>
    <link:label id="lab_us-gaap_EmployeeStockOptionMember_label_en-US" xlink:label="lab_us-gaap_EmployeeStockOptionMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Share-Based Payment Arrangement, Option [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EmployeeStockOptionMember" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_EmployeeStockOptionMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EmployeeStockOptionMember" xlink:to="lab_us-gaap_EmployeeStockOptionMember" xlink:type="arc" order="1"/>
    <link:label id="lab_stpr_MO_cc54d2d9-aff3-4b10-8146-502d6f567170_terseLabel_en-US" xlink:label="lab_stpr_MO" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Indiana</link:label>
    <link:label id="lab_stpr_MO_label_en-US" xlink:label="lab_stpr_MO" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">MISSOURI</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_stpr_MO" xlink:href="https://xbrl.sec.gov/stpr/2022/stpr-2022.xsd#stpr_MO"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_stpr_MO" xlink:to="lab_stpr_MO" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_StockIssuedDuringPeriodValueStockOptionsExercised_eaf920a9-b4c2-4545-8a70-9708ccffdfdb_terseLabel_en-US" xlink:label="lab_us-gaap_StockIssuedDuringPeriodValueStockOptionsExercised" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Common stock&#8212;option exercises and restricted stock units vesting, net of shares withheld for employee taxes</link:label>
    <link:label id="lab_us-gaap_StockIssuedDuringPeriodValueStockOptionsExercised_label_en-US" xlink:label="lab_us-gaap_StockIssuedDuringPeriodValueStockOptionsExercised" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Stock Issued During Period, Value, Stock Options Exercised</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_StockIssuedDuringPeriodValueStockOptionsExercised" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_StockIssuedDuringPeriodValueStockOptionsExercised"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_StockIssuedDuringPeriodValueStockOptionsExercised" xlink:to="lab_us-gaap_StockIssuedDuringPeriodValueStockOptionsExercised" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsForfeitedInPeriod_d201d422-310e-4868-85bd-f1d64344b2de_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsForfeitedInPeriod" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Forfeited, expired or canceled (in shares)</link:label>
    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsForfeitedInPeriod_label_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsForfeitedInPeriod" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Share-Based Compensation Arrangement by Share-Based Payment Award, Equity Instruments Other than Options, Forfeited in Period</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsForfeitedInPeriod" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsForfeitedInPeriod"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsForfeitedInPeriod" xlink:to="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsForfeitedInPeriod" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LongTermDebt_4b59a094-7e49-41ee-9bd1-b3919632d95f_verboseLabel_en-US" xlink:label="lab_us-gaap_LongTermDebt" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Long-term debt and warrants</link:label>
    <link:label id="lab_us-gaap_LongTermDebt_374591e9-3701-4109-aadc-cf96b4ce3543_totalLabel_en-US" xlink:label="lab_us-gaap_LongTermDebt" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Total</link:label>
    <link:label id="lab_us-gaap_LongTermDebt_label_en-US" xlink:label="lab_us-gaap_LongTermDebt" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Long-Term Debt</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LongTermDebt" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_LongTermDebt"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LongTermDebt" xlink:to="lab_us-gaap_LongTermDebt" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_RestructuringAndRelatedActivitiesDisclosureTextBlock_c57af314-38df-42d1-930a-b581c7116513_terseLabel_en-US" xlink:label="lab_us-gaap_RestructuringAndRelatedActivitiesDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">RESTRUCTURING COSTS</link:label>
    <link:label id="lab_us-gaap_RestructuringAndRelatedActivitiesDisclosureTextBlock_label_en-US" xlink:label="lab_us-gaap_RestructuringAndRelatedActivitiesDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Restructuring and Related Activities Disclosure [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_RestructuringAndRelatedActivitiesDisclosureTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_RestructuringAndRelatedActivitiesDisclosureTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_RestructuringAndRelatedActivitiesDisclosureTextBlock" xlink:to="lab_us-gaap_RestructuringAndRelatedActivitiesDisclosureTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CommonStockSharesAuthorized_71f98ca9-1a21-419e-9709-1cf6e1863873_terseLabel_en-US" xlink:label="lab_us-gaap_CommonStockSharesAuthorized" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Common stock, shares authorized (in shares)</link:label>
    <link:label id="lab_us-gaap_CommonStockSharesAuthorized_label_en-US" xlink:label="lab_us-gaap_CommonStockSharesAuthorized" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Common Stock, Shares Authorized</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CommonStockSharesAuthorized" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_CommonStockSharesAuthorized"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CommonStockSharesAuthorized" xlink:to="lab_us-gaap_CommonStockSharesAuthorized" xlink:type="arc" order="1"/>
    <link:label id="lab_root_CarvanaMember_5f09ea86-c019-4fb8-9c49-a56546bc1c6a_terseLabel_en-US" xlink:label="lab_root_CarvanaMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Carvana</link:label>
    <link:label id="lab_root_CarvanaMember_label_en-US" xlink:label="lab_root_CarvanaMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Carvana [Member]</link:label>
    <link:label id="lab_root_CarvanaMember_documentation_en-US" xlink:label="lab_root_CarvanaMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Carvana</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_root_CarvanaMember" xlink:href="root-20220930.xsd#root_CarvanaMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_root_CarvanaMember" xlink:to="lab_root_CarvanaMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_OtherInvestmentCompaniesMember_e2c81cd3-d2f6-4f01-9e26-7729dd907530_terseLabel_en-US" xlink:label="lab_us-gaap_OtherInvestmentCompaniesMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Other investments</link:label>
    <link:label id="lab_us-gaap_OtherInvestmentCompaniesMember_3fd4f73a-2693-4716-b518-fc78a05aabdb_verboseLabel_en-US" xlink:label="lab_us-gaap_OtherInvestmentCompaniesMember" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Other investments</link:label>
    <link:label id="lab_us-gaap_OtherInvestmentCompaniesMember_label_en-US" xlink:label="lab_us-gaap_OtherInvestmentCompaniesMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Other Investment Companies [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OtherInvestmentCompaniesMember" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_OtherInvestmentCompaniesMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_OtherInvestmentCompaniesMember" xlink:to="lab_us-gaap_OtherInvestmentCompaniesMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ClassOfWarrantOrRightAxis_27c8e3e4-83ea-4c5a-a2ac-71927e1c65b4_terseLabel_en-US" xlink:label="lab_us-gaap_ClassOfWarrantOrRightAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Class of Warrant or Right [Axis]</link:label>
    <link:label id="lab_us-gaap_ClassOfWarrantOrRightAxis_label_en-US" xlink:label="lab_us-gaap_ClassOfWarrantOrRightAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Class of Warrant or Right [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ClassOfWarrantOrRightAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ClassOfWarrantOrRightAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ClassOfWarrantOrRightAxis" xlink:to="lab_us-gaap_ClassOfWarrantOrRightAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_OperatingExpenses_51e50374-a958-4301-9fdc-b23f4fabaaae_totalLabel_en-US" xlink:label="lab_us-gaap_OperatingExpenses" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Total operating expenses</link:label>
    <link:label id="lab_us-gaap_OperatingExpenses_label_en-US" xlink:label="lab_us-gaap_OperatingExpenses" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Operating Expenses</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OperatingExpenses" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_OperatingExpenses"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_OperatingExpenses" xlink:to="lab_us-gaap_OperatingExpenses" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_MaximumMember_a7144d6e-2d04-4807-8b97-d183262e38b2_terseLabel_en-US" xlink:label="lab_srt_MaximumMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Maximum</link:label>
    <link:label id="lab_srt_MaximumMember_label_en-US" xlink:label="lab_srt_MaximumMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Maximum [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_MaximumMember" xlink:href="https://xbrl.fasb.org/srt/2022/elts/srt-2022.xsd#srt_MaximumMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_MaximumMember" xlink:to="lab_srt_MaximumMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AccumulatedOtherComprehensiveIncomeLossNetOfTax_c1b66360-5727-4562-a94d-392509fa0464_terseLabel_en-US" xlink:label="lab_us-gaap_AccumulatedOtherComprehensiveIncomeLossNetOfTax" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Accumulated other comprehensive (loss) income</link:label>
    <link:label id="lab_us-gaap_AccumulatedOtherComprehensiveIncomeLossNetOfTax_label_en-US" xlink:label="lab_us-gaap_AccumulatedOtherComprehensiveIncomeLossNetOfTax" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Accumulated Other Comprehensive Income (Loss), Net of Tax</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AccumulatedOtherComprehensiveIncomeLossNetOfTax" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_AccumulatedOtherComprehensiveIncomeLossNetOfTax"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AccumulatedOtherComprehensiveIncomeLossNetOfTax" xlink:to="lab_us-gaap_AccumulatedOtherComprehensiveIncomeLossNetOfTax" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EffectsOfReinsuranceTable_a52d6549-d2c7-4a4e-9acb-61e8ac590cfe_terseLabel_en-US" xlink:label="lab_us-gaap_EffectsOfReinsuranceTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Effects of Reinsurance [Table]</link:label>
    <link:label id="lab_us-gaap_EffectsOfReinsuranceTable_label_en-US" xlink:label="lab_us-gaap_EffectsOfReinsuranceTable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Effects of Reinsurance [Table]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EffectsOfReinsuranceTable" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_EffectsOfReinsuranceTable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EffectsOfReinsuranceTable" xlink:to="lab_us-gaap_EffectsOfReinsuranceTable" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CommonClassAMember_1ad15df1-ce16-437f-b0b0-b99cb7b999c0_terseLabel_en-US" xlink:label="lab_us-gaap_CommonClassAMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Class A Shares</link:label>
    <link:label id="lab_us-gaap_CommonClassAMember_label_en-US" xlink:label="lab_us-gaap_CommonClassAMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Common Class A [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CommonClassAMember" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_CommonClassAMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CommonClassAMember" xlink:to="lab_us-gaap_CommonClassAMember" xlink:type="arc" order="1"/>
    <link:label id="lab_stpr_NV_c5bcc66e-2668-4857-9f1e-c58f0db77730_terseLabel_en-US" xlink:label="lab_stpr_NV" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Nevada</link:label>
    <link:label id="lab_stpr_NV_label_en-US" xlink:label="lab_stpr_NV" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">NEVADA</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_stpr_NV" xlink:href="https://xbrl.sec.gov/stpr/2022/stpr-2022.xsd#stpr_NV"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_stpr_NV" xlink:to="lab_stpr_NV" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CashAndCashEquivalentsAtCarryingValue_55546293-d6f9-4b50-a561-6c6c4e0706aa_terseLabel_en-US" xlink:label="lab_us-gaap_CashAndCashEquivalentsAtCarryingValue" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Cash and cash equivalents</link:label>
    <link:label id="lab_us-gaap_CashAndCashEquivalentsAtCarryingValue_c802bf01-afad-4a90-b9d4-b0471daea22d_verboseLabel_en-US" xlink:label="lab_us-gaap_CashAndCashEquivalentsAtCarryingValue" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Cash and cash equivalents</link:label>
    <link:label id="lab_us-gaap_CashAndCashEquivalentsAtCarryingValue_label_en-US" xlink:label="lab_us-gaap_CashAndCashEquivalentsAtCarryingValue" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Cash and Cash Equivalents, at Carrying Value</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CashAndCashEquivalentsAtCarryingValue" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_CashAndCashEquivalentsAtCarryingValue"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CashAndCashEquivalentsAtCarryingValue" xlink:to="lab_us-gaap_CashAndCashEquivalentsAtCarryingValue" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EquitySecuritiesFvNiGainLoss_7e8efeab-4502-4cb4-8b2c-eac502398f30_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_EquitySecuritiesFvNiGainLoss" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Change in fair value of equity securities</link:label>
    <link:label id="lab_us-gaap_EquitySecuritiesFvNiGainLoss_label_en-US" xlink:label="lab_us-gaap_EquitySecuritiesFvNiGainLoss" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Equity Securities, FV-NI, Gain (Loss)</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EquitySecuritiesFvNiGainLoss" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_EquitySecuritiesFvNiGainLoss"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EquitySecuritiesFvNiGainLoss" xlink:to="lab_us-gaap_EquitySecuritiesFvNiGainLoss" xlink:type="arc" order="1"/>
    <link:label id="lab_root_SoftwareCostsMember_6d54e9c4-ccf1-4160-b077-20484652c736_terseLabel_en-US" xlink:label="lab_root_SoftwareCostsMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Software costs</link:label>
    <link:label id="lab_root_SoftwareCostsMember_label_en-US" xlink:label="lab_root_SoftwareCostsMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Software Costs [Member]</link:label>
    <link:label id="lab_root_SoftwareCostsMember_documentation_en-US" xlink:label="lab_root_SoftwareCostsMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Software Costs</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_root_SoftwareCostsMember" xlink:href="root-20220930.xsd#root_SoftwareCostsMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_root_SoftwareCostsMember" xlink:to="lab_root_SoftwareCostsMember" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_EntitySmallBusiness_9690d5b8-a731-4aa8-ae6c-847d8605c0c9_terseLabel_en-US" xlink:label="lab_dei_EntitySmallBusiness" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Entity Small Business</link:label>
    <link:label id="lab_dei_EntitySmallBusiness_label_en-US" xlink:label="lab_dei_EntitySmallBusiness" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Entity Small Business</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_EntitySmallBusiness" xlink:href="https://xbrl.sec.gov/dei/2022/dei-2022.xsd#dei_EntitySmallBusiness"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_EntitySmallBusiness" xlink:to="lab_dei_EntitySmallBusiness" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FairValueByMeasurementBasisAxis_0b010256-c9da-4233-922e-167d80872a2f_terseLabel_en-US" xlink:label="lab_us-gaap_FairValueByMeasurementBasisAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Measurement Basis [Axis]</link:label>
    <link:label id="lab_us-gaap_FairValueByMeasurementBasisAxis_label_en-US" xlink:label="lab_us-gaap_FairValueByMeasurementBasisAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Measurement Basis [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueByMeasurementBasisAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_FairValueByMeasurementBasisAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FairValueByMeasurementBasisAxis" xlink:to="lab_us-gaap_FairValueByMeasurementBasisAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ScheduleOfStockholdersEquityNoteWarrantsOrRightsTextBlock_cc9d120c-873b-46fc-b09c-dfc29fdb7f41_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfStockholdersEquityNoteWarrantsOrRightsTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Schedule of Stockholders' Equity Note, Warrants or Rights</link:label>
    <link:label id="lab_us-gaap_ScheduleOfStockholdersEquityNoteWarrantsOrRightsTextBlock_label_en-US" xlink:label="lab_us-gaap_ScheduleOfStockholdersEquityNoteWarrantsOrRightsTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Schedule of Stockholders' Equity Note, Warrants or Rights [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfStockholdersEquityNoteWarrantsOrRightsTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ScheduleOfStockholdersEquityNoteWarrantsOrRightsTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ScheduleOfStockholdersEquityNoteWarrantsOrRightsTextBlock" xlink:to="lab_us-gaap_ScheduleOfStockholdersEquityNoteWarrantsOrRightsTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_RevenuesAbstract_2b730d93-388c-4392-bd12-b897994b23bb_terseLabel_en-US" xlink:label="lab_us-gaap_RevenuesAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Revenues:</link:label>
    <link:label id="lab_us-gaap_RevenuesAbstract_label_en-US" xlink:label="lab_us-gaap_RevenuesAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Revenues [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_RevenuesAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_RevenuesAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_RevenuesAbstract" xlink:to="lab_us-gaap_RevenuesAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_RestrictedCash_18ada8cf-a4bf-4093-8c88-25d10213c905_terseLabel_en-US" xlink:label="lab_us-gaap_RestrictedCash" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Restricted cash</link:label>
    <link:label id="lab_us-gaap_RestrictedCash_c33da47b-f8b4-44f3-a300-f5d38dc485d1_verboseLabel_en-US" xlink:label="lab_us-gaap_RestrictedCash" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Restricted cash</link:label>
    <link:label id="lab_us-gaap_RestrictedCash_label_en-US" xlink:label="lab_us-gaap_RestrictedCash" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Restricted Cash</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_RestrictedCash" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_RestrictedCash"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_RestrictedCash" xlink:to="lab_us-gaap_RestrictedCash" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_PaymentsToAcquireAvailableForSaleSecuritiesDebt_ad5b67b4-99eb-4f7d-aeaf-7895048ccaf0_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_PaymentsToAcquireAvailableForSaleSecuritiesDebt" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Purchases of investments</link:label>
    <link:label id="lab_us-gaap_PaymentsToAcquireAvailableForSaleSecuritiesDebt_label_en-US" xlink:label="lab_us-gaap_PaymentsToAcquireAvailableForSaleSecuritiesDebt" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Payments to Acquire Debt Securities, Available-for-Sale</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PaymentsToAcquireAvailableForSaleSecuritiesDebt" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_PaymentsToAcquireAvailableForSaleSecuritiesDebt"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PaymentsToAcquireAvailableForSaleSecuritiesDebt" xlink:to="lab_us-gaap_PaymentsToAcquireAvailableForSaleSecuritiesDebt" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_SignificantAccountingPoliciesTextBlock_3172abf7-f22c-40c7-b121-af5cdade3316_terseLabel_en-US" xlink:label="lab_us-gaap_SignificantAccountingPoliciesTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">BASIS OF PRESENTATION AND SUMMARY OF SIGNIFICANT ACCOUNTING POLICIES</link:label>
    <link:label id="lab_us-gaap_SignificantAccountingPoliciesTextBlock_label_en-US" xlink:label="lab_us-gaap_SignificantAccountingPoliciesTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Significant Accounting Policies [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SignificantAccountingPoliciesTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_SignificantAccountingPoliciesTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_SignificantAccountingPoliciesTextBlock" xlink:to="lab_us-gaap_SignificantAccountingPoliciesTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_PremiumsEarnedNet_01dd1203-01f9-442d-a50c-d5020d64ac1b_terseLabel_en-US" xlink:label="lab_us-gaap_PremiumsEarnedNet" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Net premiums earned</link:label>
    <link:label id="lab_us-gaap_PremiumsEarnedNet_b7f13df0-afd6-4fed-846d-afc0fdd20d88_totalLabel_en-US" xlink:label="lab_us-gaap_PremiumsEarnedNet" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Net premiums earned</link:label>
    <link:label id="lab_us-gaap_PremiumsEarnedNet_label_en-US" xlink:label="lab_us-gaap_PremiumsEarnedNet" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Premiums Earned, Net</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PremiumsEarnedNet" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_PremiumsEarnedNet"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PremiumsEarnedNet" xlink:to="lab_us-gaap_PremiumsEarnedNet" xlink:type="arc" order="1"/>
    <link:label id="lab_stpr_LA_01aa0caf-bfc3-4a28-8d12-8bb12162dfc5_terseLabel_en-US" xlink:label="lab_stpr_LA" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Louisiana</link:label>
    <link:label id="lab_stpr_LA_label_en-US" xlink:label="lab_stpr_LA" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">LOUISIANA</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_stpr_LA" xlink:href="https://xbrl.sec.gov/stpr/2022/stpr-2022.xsd#stpr_LA"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_stpr_LA" xlink:to="lab_stpr_LA" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardOptionsOutstandingRollForward_005e5392-cca2-4829-a130-285817fff85d_terseLabel_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardOptionsOutstandingRollForward" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Number of Shares</link:label>
    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardOptionsOutstandingRollForward_label_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardOptionsOutstandingRollForward" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Share-Based Compensation Arrangement by Share-Based Payment Award, Options, Outstanding [Roll Forward]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardOptionsOutstandingRollForward" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardOptionsOutstandingRollForward"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardOptionsOutstandingRollForward" xlink:to="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardOptionsOutstandingRollForward" xlink:type="arc" order="1"/>
    <link:label id="lab_root_RootInsuranceCompanyMember_73200126-4fac-40aa-aeb6-8208c246c008_terseLabel_en-US" xlink:label="lab_root_RootInsuranceCompanyMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Root Insurance Company</link:label>
    <link:label id="lab_root_RootInsuranceCompanyMember_label_en-US" xlink:label="lab_root_RootInsuranceCompanyMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Root Insurance Company [Member]</link:label>
    <link:label id="lab_root_RootInsuranceCompanyMember_documentation_en-US" xlink:label="lab_root_RootInsuranceCompanyMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Root Insurance Company</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_root_RootInsuranceCompanyMember" xlink:href="root-20220930.xsd#root_RootInsuranceCompanyMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_root_RootInsuranceCompanyMember" xlink:to="lab_root_RootInsuranceCompanyMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_PaidInKindInterest_afa163f9-372c-41d8-a7af-dd0bdf9dada1_terseLabel_en-US" xlink:label="lab_us-gaap_PaidInKindInterest" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Payment-in-kind interest expense</link:label>
    <link:label id="lab_us-gaap_PaidInKindInterest_label_en-US" xlink:label="lab_us-gaap_PaidInKindInterest" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Paid-in-Kind Interest</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PaidInKindInterest" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_PaidInKindInterest"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PaidInKindInterest" xlink:to="lab_us-gaap_PaidInKindInterest" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardOptionsOutstandingIntrinsicValue_32e67aff-f7aa-4e86-9723-c694c29a0378_terseLabel_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardOptionsOutstandingIntrinsicValue" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Outstanding, aggregate intrinsic value</link:label>
    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardOptionsOutstandingIntrinsicValue_label_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardOptionsOutstandingIntrinsicValue" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Share-Based Compensation Arrangement by Share-Based Payment Award, Options, Outstanding, Intrinsic Value</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardOptionsOutstandingIntrinsicValue" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardOptionsOutstandingIntrinsicValue"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardOptionsOutstandingIntrinsicValue" xlink:to="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardOptionsOutstandingIntrinsicValue" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_Security12bTitle_a2d26b62-4d0b-488d-8f8e-890244176482_terseLabel_en-US" xlink:label="lab_dei_Security12bTitle" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Title of 12(b) Security</link:label>
    <link:label id="lab_dei_Security12bTitle_label_en-US" xlink:label="lab_dei_Security12bTitle" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Title of 12(b) Security</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_Security12bTitle" xlink:href="https://xbrl.sec.gov/dei/2022/dei-2022.xsd#dei_Security12bTitle"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_Security12bTitle" xlink:to="lab_dei_Security12bTitle" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_BondsMember_ec6e1cf7-faee-4088-84a9-9ced2ed62079_terseLabel_en-US" xlink:label="lab_us-gaap_BondsMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Interest on bonds</link:label>
    <link:label id="lab_us-gaap_BondsMember_label_en-US" xlink:label="lab_us-gaap_BondsMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Bonds [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_BondsMember" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_BondsMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_BondsMember" xlink:to="lab_us-gaap_BondsMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ConversionOfStockSharesIssued1_6c34e1d1-2d42-4a5f-b923-95c9c84e7fc7_terseLabel_en-US" xlink:label="lab_us-gaap_ConversionOfStockSharesIssued1" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Conversion of stock, shares issued</link:label>
    <link:label id="lab_us-gaap_ConversionOfStockSharesIssued1_label_en-US" xlink:label="lab_us-gaap_ConversionOfStockSharesIssued1" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Conversion of Stock, Shares Issued</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ConversionOfStockSharesIssued1" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ConversionOfStockSharesIssued1"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ConversionOfStockSharesIssued1" xlink:to="lab_us-gaap_ConversionOfStockSharesIssued1" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_SubsequentEventLineItems_30dbf507-9ed1-4cf0-a1a8-fb0c046ed089_terseLabel_en-US" xlink:label="lab_us-gaap_SubsequentEventLineItems" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Subsequent Event [Line Items]</link:label>
    <link:label id="lab_us-gaap_SubsequentEventLineItems_label_en-US" xlink:label="lab_us-gaap_SubsequentEventLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Subsequent Event [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SubsequentEventLineItems" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_SubsequentEventLineItems"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_SubsequentEventLineItems" xlink:to="lab_us-gaap_SubsequentEventLineItems" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DebtInstrumentLineItems_9e2a2f91-345d-4357-96cd-7012c90d19f7_terseLabel_en-US" xlink:label="lab_us-gaap_DebtInstrumentLineItems" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt Instrument [Line Items]</link:label>
    <link:label id="lab_us-gaap_DebtInstrumentLineItems_label_en-US" xlink:label="lab_us-gaap_DebtInstrumentLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt Instrument [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtInstrumentLineItems" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_DebtInstrumentLineItems"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DebtInstrumentLineItems" xlink:to="lab_us-gaap_DebtInstrumentLineItems" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_InterestPayableCurrentAndNoncurrent_7db793e2-20b4-4d16-8499-ea89af989acd_terseLabel_en-US" xlink:label="lab_us-gaap_InterestPayableCurrentAndNoncurrent" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Accrued interest payable</link:label>
    <link:label id="lab_us-gaap_InterestPayableCurrentAndNoncurrent_label_en-US" xlink:label="lab_us-gaap_InterestPayableCurrentAndNoncurrent" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Interest Payable</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_InterestPayableCurrentAndNoncurrent" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_InterestPayableCurrentAndNoncurrent"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_InterestPayableCurrentAndNoncurrent" xlink:to="lab_us-gaap_InterestPayableCurrentAndNoncurrent" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPositionLessThan12MonthsAccumulatedLoss_9fc0b462-ff15-41c0-8131-9433867f2caf_negatedLabel_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPositionLessThan12MonthsAccumulatedLoss" xlink:role="http://www.xbrl.org/2009/role/negatedLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Less than 12 months, unrealized loss</link:label>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPositionLessThan12MonthsAccumulatedLoss_label_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPositionLessThan12MonthsAccumulatedLoss" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt Securities, Available-for-Sale, Continuous Unrealized Loss Position, Less than 12 Months, Accumulated Loss</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPositionLessThan12MonthsAccumulatedLoss" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPositionLessThan12MonthsAccumulatedLoss"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPositionLessThan12MonthsAccumulatedLoss" xlink:to="lab_us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPositionLessThan12MonthsAccumulatedLoss" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ClassOfStockLineItems_3a6b3a83-6892-4a2b-aae7-83ccf5b3227b_terseLabel_en-US" xlink:label="lab_us-gaap_ClassOfStockLineItems" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Class of Stock [Line Items]</link:label>
    <link:label id="lab_us-gaap_ClassOfStockLineItems_label_en-US" xlink:label="lab_us-gaap_ClassOfStockLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Class of Stock [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ClassOfStockLineItems" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ClassOfStockLineItems"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ClassOfStockLineItems" xlink:to="lab_us-gaap_ClassOfStockLineItems" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ReinsuranceRecoverablesOnPaidAndUnpaidLosses_40823bf0-3c9c-4cae-b7bd-28bd26b33b33_terseLabel_en-US" xlink:label="lab_us-gaap_ReinsuranceRecoverablesOnPaidAndUnpaidLosses" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Reinsurance recoverable and receivable, net of allowance of $0.1 and $0.2 at September&#160;30, 2022 and December&#160;31, 2021, respectively</link:label>
    <link:label id="lab_us-gaap_ReinsuranceRecoverablesOnPaidAndUnpaidLosses_label_en-US" xlink:label="lab_us-gaap_ReinsuranceRecoverablesOnPaidAndUnpaidLosses" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Reinsurance Recoverable for Paid and Unpaid Claims and Claims Adjustments</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ReinsuranceRecoverablesOnPaidAndUnpaidLosses" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ReinsuranceRecoverablesOnPaidAndUnpaidLosses"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ReinsuranceRecoverablesOnPaidAndUnpaidLosses" xlink:to="lab_us-gaap_ReinsuranceRecoverablesOnPaidAndUnpaidLosses" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_InvestmentsDebtAndEquitySecuritiesAbstract_label_en-US" xlink:label="lab_us-gaap_InvestmentsDebtAndEquitySecuritiesAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Investments, Debt and Equity Securities [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_InvestmentsDebtAndEquitySecuritiesAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_InvestmentsDebtAndEquitySecuritiesAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_InvestmentsDebtAndEquitySecuritiesAbstract" xlink:to="lab_us-gaap_InvestmentsDebtAndEquitySecuritiesAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_root_TechnologyAndDevelopmentExpense_442d0fdb-f2bf-4e01-b653-d8972aa40700_terseLabel_en-US" xlink:label="lab_root_TechnologyAndDevelopmentExpense" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Technology and development</link:label>
    <link:label id="lab_root_TechnologyAndDevelopmentExpense_label_en-US" xlink:label="lab_root_TechnologyAndDevelopmentExpense" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Technology And Development Expense</link:label>
    <link:label id="lab_root_TechnologyAndDevelopmentExpense_documentation_en-US" xlink:label="lab_root_TechnologyAndDevelopmentExpense" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Technology And Development Expense</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_root_TechnologyAndDevelopmentExpense" xlink:href="root-20220930.xsd#root_TechnologyAndDevelopmentExpense"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_root_TechnologyAndDevelopmentExpense" xlink:to="lab_root_TechnologyAndDevelopmentExpense" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPosition12MonthsOrLongerAccumulatedLoss_29840311-3af0-46c8-8d86-08fd712c2055_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPosition12MonthsOrLongerAccumulatedLoss" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">12 months or more, unrealized loss</link:label>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPosition12MonthsOrLongerAccumulatedLoss_label_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPosition12MonthsOrLongerAccumulatedLoss" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt Securities, Available-for-Sale, Continuous Unrealized Loss Position, 12 Months or Longer, Accumulated Loss</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPosition12MonthsOrLongerAccumulatedLoss" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPosition12MonthsOrLongerAccumulatedLoss"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPosition12MonthsOrLongerAccumulatedLoss" xlink:to="lab_us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPosition12MonthsOrLongerAccumulatedLoss" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LiabilitiesAndStockholdersEquityAbstract_f3388532-a17f-4d41-9865-ee049e29dd66_terseLabel_en-US" xlink:label="lab_us-gaap_LiabilitiesAndStockholdersEquityAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Liabilities, Redeemable Convertible Preferred Stock and Stockholders&#8217; Equity</link:label>
    <link:label id="lab_us-gaap_LiabilitiesAndStockholdersEquityAbstract_label_en-US" xlink:label="lab_us-gaap_LiabilitiesAndStockholdersEquityAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Liabilities and Equity [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LiabilitiesAndStockholdersEquityAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_LiabilitiesAndStockholdersEquityAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LiabilitiesAndStockholdersEquityAbstract" xlink:to="lab_us-gaap_LiabilitiesAndStockholdersEquityAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EstimateOfFairValueFairValueDisclosureMember_a18f95b9-793b-41ff-812a-83e31f51e225_terseLabel_en-US" xlink:label="lab_us-gaap_EstimateOfFairValueFairValueDisclosureMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Estimated Fair Value</link:label>
    <link:label id="lab_us-gaap_EstimateOfFairValueFairValueDisclosureMember_label_en-US" xlink:label="lab_us-gaap_EstimateOfFairValueFairValueDisclosureMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Estimate of Fair Value Measurement [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EstimateOfFairValueFairValueDisclosureMember" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_EstimateOfFairValueFairValueDisclosureMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EstimateOfFairValueFairValueDisclosureMember" xlink:to="lab_us-gaap_EstimateOfFairValueFairValueDisclosureMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementsByShareBasedPaymentAwardOptionsGrantsInPeriodWeightedAverageExercisePrice_2ba7fa4e-973d-4c9e-82f0-8f602f86fa4e_terseLabel_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementsByShareBasedPaymentAwardOptionsGrantsInPeriodWeightedAverageExercisePrice" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Granted, weighted-average exercise price (in dollars per share)</link:label>
    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementsByShareBasedPaymentAwardOptionsGrantsInPeriodWeightedAverageExercisePrice_label_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementsByShareBasedPaymentAwardOptionsGrantsInPeriodWeightedAverageExercisePrice" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Share-Based Compensation Arrangements by Share-Based Payment Award, Options, Grants in Period, Weighted Average Exercise Price</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShareBasedCompensationArrangementsByShareBasedPaymentAwardOptionsGrantsInPeriodWeightedAverageExercisePrice" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ShareBasedCompensationArrangementsByShareBasedPaymentAwardOptionsGrantsInPeriodWeightedAverageExercisePrice"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ShareBasedCompensationArrangementsByShareBasedPaymentAwardOptionsGrantsInPeriodWeightedAverageExercisePrice" xlink:to="lab_us-gaap_ShareBasedCompensationArrangementsByShareBasedPaymentAwardOptionsGrantsInPeriodWeightedAverageExercisePrice" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AvailableForSaleDebtSecuritiesAmortizedCostBasis_7092f35b-33be-4858-8d8a-b379113a9274_totalLabel_en-US" xlink:label="lab_us-gaap_AvailableForSaleDebtSecuritiesAmortizedCostBasis" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Amortized Cost</link:label>
    <link:label id="lab_us-gaap_AvailableForSaleDebtSecuritiesAmortizedCostBasis_bea28916-e5c9-44d6-b13a-a780493c2812_terseLabel_en-US" xlink:label="lab_us-gaap_AvailableForSaleDebtSecuritiesAmortizedCostBasis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Amortized Cost</link:label>
    <link:label id="lab_us-gaap_AvailableForSaleDebtSecuritiesAmortizedCostBasis_label_en-US" xlink:label="lab_us-gaap_AvailableForSaleDebtSecuritiesAmortizedCostBasis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt Securities, Available-for-Sale, Amortized Cost</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AvailableForSaleDebtSecuritiesAmortizedCostBasis" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_AvailableForSaleDebtSecuritiesAmortizedCostBasis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AvailableForSaleDebtSecuritiesAmortizedCostBasis" xlink:to="lab_us-gaap_AvailableForSaleDebtSecuritiesAmortizedCostBasis" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardOptionsForfeituresAndExpirationsInPeriodWeightedAverageExercisePrice_d1ba2abd-0c8e-4b76-8e48-39fbcd25f7f7_terseLabel_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardOptionsForfeituresAndExpirationsInPeriodWeightedAverageExercisePrice" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Forfeited, expired and canceled, weighted-average exercise price (in dollars per share)</link:label>
    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardOptionsForfeituresAndExpirationsInPeriodWeightedAverageExercisePrice_label_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardOptionsForfeituresAndExpirationsInPeriodWeightedAverageExercisePrice" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Share-Based Compensation Arrangement by Share-Based Payment Award, Options, Forfeitures and Expirations in Period, Weighted Average Exercise Price</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardOptionsForfeituresAndExpirationsInPeriodWeightedAverageExercisePrice" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardOptionsForfeituresAndExpirationsInPeriodWeightedAverageExercisePrice"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardOptionsForfeituresAndExpirationsInPeriodWeightedAverageExercisePrice" xlink:to="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardOptionsForfeituresAndExpirationsInPeriodWeightedAverageExercisePrice" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersCurrentYearClaimsAndClaimsAdjustmentExpense_ec944b93-dd3d-48bb-b449-d9662e731eab_terseLabel_en-US" xlink:label="lab_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersCurrentYearClaimsAndClaimsAdjustmentExpense" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Current year</link:label>
    <link:label id="lab_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersCurrentYearClaimsAndClaimsAdjustmentExpense_label_en-US" xlink:label="lab_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersCurrentYearClaimsAndClaimsAdjustmentExpense" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Current Year Claims and Claims Adjustment Expense</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersCurrentYearClaimsAndClaimsAdjustmentExpense" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersCurrentYearClaimsAndClaimsAdjustmentExpense"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersCurrentYearClaimsAndClaimsAdjustmentExpense" xlink:to="lab_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersCurrentYearClaimsAndClaimsAdjustmentExpense" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_RestructuringCharges_d2d1d0cd-9fa7-445d-906e-f62ee605215a_terseLabel_en-US" xlink:label="lab_us-gaap_RestructuringCharges" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Severance, benefits, and related costs</link:label>
    <link:label id="lab_us-gaap_RestructuringCharges_label_en-US" xlink:label="lab_us-gaap_RestructuringCharges" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Restructuring Charges</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_RestructuringCharges" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_RestructuringCharges"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_RestructuringCharges" xlink:to="lab_us-gaap_RestructuringCharges" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_IncreaseDecreaseInOtherOperatingAssets_23aa824b-8879-48da-b203-58e971c6ea24_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_IncreaseDecreaseInOtherOperatingAssets" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Other assets</link:label>
    <link:label id="lab_us-gaap_IncreaseDecreaseInOtherOperatingAssets_label_en-US" xlink:label="lab_us-gaap_IncreaseDecreaseInOtherOperatingAssets" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Increase (Decrease) in Other Operating Assets</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncreaseDecreaseInOtherOperatingAssets" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_IncreaseDecreaseInOtherOperatingAssets"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IncreaseDecreaseInOtherOperatingAssets" xlink:to="lab_us-gaap_IncreaseDecreaseInOtherOperatingAssets" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_CreditRatingStandardPoorsAxis_3e5d19a6-ec6a-4af1-abae-f0cea7c5221f_terseLabel_en-US" xlink:label="lab_srt_CreditRatingStandardPoorsAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Credit Rating, Standard &amp; Poor's [Axis]</link:label>
    <link:label id="lab_srt_CreditRatingStandardPoorsAxis_label_en-US" xlink:label="lab_srt_CreditRatingStandardPoorsAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Credit Rating, Standard &amp; Poor's [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_CreditRatingStandardPoorsAxis" xlink:href="https://xbrl.fasb.org/srt/2022/elts/srt-2022.xsd#srt_CreditRatingStandardPoorsAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_CreditRatingStandardPoorsAxis" xlink:to="lab_srt_CreditRatingStandardPoorsAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_NatureOfOperations_bb52fe82-75a7-4cfe-a60a-e90643e8dd97_terseLabel_en-US" xlink:label="lab_us-gaap_NatureOfOperations" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">NATURE OF BUSINESS</link:label>
    <link:label id="lab_us-gaap_NatureOfOperations_label_en-US" xlink:label="lab_us-gaap_NatureOfOperations" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Nature of Operations [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NatureOfOperations" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_NatureOfOperations"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_NatureOfOperations" xlink:to="lab_us-gaap_NatureOfOperations" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_WarrantMember_76426285-2733-41db-999a-844abc0f61b0_terseLabel_en-US" xlink:label="lab_us-gaap_WarrantMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Warrant</link:label>
    <link:label id="lab_us-gaap_WarrantMember_60d54c3f-06a7-4a00-a672-6728694d1b81_verboseLabel_en-US" xlink:label="lab_us-gaap_WarrantMember" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Warrants to purchase common stock</link:label>
    <link:label id="lab_us-gaap_WarrantMember_label_en-US" xlink:label="lab_us-gaap_WarrantMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Warrant [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_WarrantMember" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_WarrantMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_WarrantMember" xlink:to="lab_us-gaap_WarrantMember" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_EntityFilerCategory_22d3d782-240f-444c-9b67-28b7cdc37acf_terseLabel_en-US" xlink:label="lab_dei_EntityFilerCategory" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Entity Filer Category</link:label>
    <link:label id="lab_dei_EntityFilerCategory_label_en-US" xlink:label="lab_dei_EntityFilerCategory" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Entity Filer Category</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_EntityFilerCategory" xlink:href="https://xbrl.sec.gov/dei/2022/dei-2022.xsd#dei_EntityFilerCategory"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_EntityFilerCategory" xlink:to="lab_dei_EntityFilerCategory" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_WeightedAverageNumberOfSharesOutstandingBasic_07f31164-7f5e-45db-9b58-744600087d56_terseLabel_en-US" xlink:label="lab_us-gaap_WeightedAverageNumberOfSharesOutstandingBasic" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Weighted-average common shares outstanding: basic (both Class A and B) (in shares)</link:label>
    <link:label id="lab_us-gaap_WeightedAverageNumberOfSharesOutstandingBasic_label_en-US" xlink:label="lab_us-gaap_WeightedAverageNumberOfSharesOutstandingBasic" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Weighted Average Number of Shares Outstanding, Basic</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_WeightedAverageNumberOfSharesOutstandingBasic" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_WeightedAverageNumberOfSharesOutstandingBasic"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_WeightedAverageNumberOfSharesOutstandingBasic" xlink:to="lab_us-gaap_WeightedAverageNumberOfSharesOutstandingBasic" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ReinsurancePayable_f3f39f19-c06b-4b73-8cde-9856343193ab_terseLabel_en-US" xlink:label="lab_us-gaap_ReinsurancePayable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Reinsurance premiums payable</link:label>
    <link:label id="lab_us-gaap_ReinsurancePayable_label_en-US" xlink:label="lab_us-gaap_ReinsurancePayable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Reinsurance Payable</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ReinsurancePayable" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ReinsurancePayable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ReinsurancePayable" xlink:to="lab_us-gaap_ReinsurancePayable" xlink:type="arc" order="1"/>
    <link:label id="lab_root_DebtInstrumentCovenantComplianceMaximumMonthlyCashSpend_f38312ea-6a57-46cf-a9c7-20f6ca088a0e_terseLabel_en-US" xlink:label="lab_root_DebtInstrumentCovenantComplianceMaximumMonthlyCashSpend" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt instrument, covenant compliance, maximum monthly cash spend</link:label>
    <link:label id="lab_root_DebtInstrumentCovenantComplianceMaximumMonthlyCashSpend_label_en-US" xlink:label="lab_root_DebtInstrumentCovenantComplianceMaximumMonthlyCashSpend" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt Instrument, Covenant Compliance, Maximum Monthly Cash Spend</link:label>
    <link:label id="lab_root_DebtInstrumentCovenantComplianceMaximumMonthlyCashSpend_documentation_en-US" xlink:label="lab_root_DebtInstrumentCovenantComplianceMaximumMonthlyCashSpend" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt Instrument, Covenant Compliance, Maximum Monthly Cash Spend</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_root_DebtInstrumentCovenantComplianceMaximumMonthlyCashSpend" xlink:href="root-20220930.xsd#root_DebtInstrumentCovenantComplianceMaximumMonthlyCashSpend"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_root_DebtInstrumentCovenantComplianceMaximumMonthlyCashSpend" xlink:to="lab_root_DebtInstrumentCovenantComplianceMaximumMonthlyCashSpend" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersPriorYearClaimsAndClaimsAdjustmentExpense_f79a3193-1340-4cd4-8e20-34928a7bd87c_terseLabel_en-US" xlink:label="lab_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersPriorYearClaimsAndClaimsAdjustmentExpense" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Prior years</link:label>
    <link:label id="lab_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersPriorYearClaimsAndClaimsAdjustmentExpense_63101ba8-5a1b-4b83-a2c3-e018639a2f99_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersPriorYearClaimsAndClaimsAdjustmentExpense" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Incurred losses and LAE attributable to prior accident years</link:label>
    <link:label id="lab_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersPriorYearClaimsAndClaimsAdjustmentExpense_label_en-US" xlink:label="lab_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersPriorYearClaimsAndClaimsAdjustmentExpense" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Prior Year Claims and Claims Adjustment Expense</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersPriorYearClaimsAndClaimsAdjustmentExpense" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersPriorYearClaimsAndClaimsAdjustmentExpense"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersPriorYearClaimsAndClaimsAdjustmentExpense" xlink:to="lab_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersPriorYearClaimsAndClaimsAdjustmentExpense" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EquityMethodInvestmentOwnershipPercentage_731475de-4c0a-4b3b-ab1b-bf00e2a2b68f_terseLabel_en-US" xlink:label="lab_us-gaap_EquityMethodInvestmentOwnershipPercentage" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Ownership percentage (as percent)</link:label>
    <link:label id="lab_us-gaap_EquityMethodInvestmentOwnershipPercentage_label_en-US" xlink:label="lab_us-gaap_EquityMethodInvestmentOwnershipPercentage" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Equity Method Investment, Ownership Percentage</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EquityMethodInvestmentOwnershipPercentage" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_EquityMethodInvestmentOwnershipPercentage"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EquityMethodInvestmentOwnershipPercentage" xlink:to="lab_us-gaap_EquityMethodInvestmentOwnershipPercentage" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AllocatedShareBasedCompensationExpense_c144b3fd-d865-420e-a5c0-3069ec96a793_terseLabel_en-US" xlink:label="lab_us-gaap_AllocatedShareBasedCompensationExpense" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Total share-based compensation expense</link:label>
    <link:label id="lab_us-gaap_AllocatedShareBasedCompensationExpense_label_en-US" xlink:label="lab_us-gaap_AllocatedShareBasedCompensationExpense" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Share-Based Payment Arrangement, Expense</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AllocatedShareBasedCompensationExpense" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_AllocatedShareBasedCompensationExpense"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AllocatedShareBasedCompensationExpense" xlink:to="lab_us-gaap_AllocatedShareBasedCompensationExpense" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CommitmentsAndContingencies_00562245-21df-446d-9b64-1342d7239580_terseLabel_en-US" xlink:label="lab_us-gaap_CommitmentsAndContingencies" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Commitments and Contingencies (Note 11)</link:label>
    <link:label id="lab_us-gaap_CommitmentsAndContingencies_label_en-US" xlink:label="lab_us-gaap_CommitmentsAndContingencies" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Commitments and Contingencies</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CommitmentsAndContingencies" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_CommitmentsAndContingencies"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CommitmentsAndContingencies" xlink:to="lab_us-gaap_CommitmentsAndContingencies" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_SecurityExchangeName_2acf63b5-b4e1-4e0f-82f2-dd7c8fbd2d0e_terseLabel_en-US" xlink:label="lab_dei_SecurityExchangeName" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Security Exchange Name</link:label>
    <link:label id="lab_dei_SecurityExchangeName_label_en-US" xlink:label="lab_dei_SecurityExchangeName" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Security Exchange Name</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_SecurityExchangeName" xlink:href="https://xbrl.sec.gov/dei/2022/dei-2022.xsd#dei_SecurityExchangeName"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_SecurityExchangeName" xlink:to="lab_dei_SecurityExchangeName" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardOptionsOutstandingWeightedAverageExercisePrice_bdaadb2b-5548-41a7-9e9a-b6fa4cc25123_periodStartLabel_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardOptionsOutstandingWeightedAverageExercisePrice" xlink:role="http://www.xbrl.org/2003/role/periodStartLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Outstanding, beginning balance, weighted-average exercise price (in dollars per share)</link:label>
    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardOptionsOutstandingWeightedAverageExercisePrice_0cdc8372-86bf-4377-8414-8bb011e5b3f2_periodEndLabel_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardOptionsOutstandingWeightedAverageExercisePrice" xlink:role="http://www.xbrl.org/2003/role/periodEndLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Outstanding, ending balance, weighted-average exercise price (in dollars per share)</link:label>
    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardOptionsOutstandingWeightedAverageExercisePrice_label_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardOptionsOutstandingWeightedAverageExercisePrice" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Share-Based Compensation Arrangement by Share-Based Payment Award, Options, Outstanding, Weighted Average Exercise Price</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardOptionsOutstandingWeightedAverageExercisePrice" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardOptionsOutstandingWeightedAverageExercisePrice"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardOptionsOutstandingWeightedAverageExercisePrice" xlink:to="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardOptionsOutstandingWeightedAverageExercisePrice" xlink:type="arc" order="1"/>
    <link:label id="lab_root_GainLossOnLeaseModification_a3c502ff-2972-4f6b-b4c9-198b52d21125_negatedLabel_en-US" xlink:label="lab_root_GainLossOnLeaseModification" xlink:role="http://www.xbrl.org/2009/role/negatedLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Gain on lease modification</link:label>
    <link:label id="lab_root_GainLossOnLeaseModification_label_en-US" xlink:label="lab_root_GainLossOnLeaseModification" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Gain (Loss) On Lease Modification</link:label>
    <link:label id="lab_root_GainLossOnLeaseModification_documentation_en-US" xlink:label="lab_root_GainLossOnLeaseModification" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Gain (Loss) On Lease Modification</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_root_GainLossOnLeaseModification" xlink:href="root-20220930.xsd#root_GainLossOnLeaseModification"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_root_GainLossOnLeaseModification" xlink:to="lab_root_GainLossOnLeaseModification" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ClassOfWarrantOrRightDomain_a781f9c5-e050-4452-903d-716585819909_terseLabel_en-US" xlink:label="lab_us-gaap_ClassOfWarrantOrRightDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Class of Warrant or Right [Domain]</link:label>
    <link:label id="lab_us-gaap_ClassOfWarrantOrRightDomain_label_en-US" xlink:label="lab_us-gaap_ClassOfWarrantOrRightDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Class of Warrant or Right [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ClassOfWarrantOrRightDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ClassOfWarrantOrRightDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ClassOfWarrantOrRightDomain" xlink:to="lab_us-gaap_ClassOfWarrantOrRightDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FairValueBalanceSheetGroupingFinancialStatementCaptionsLineItems_b6905b5e-a988-4150-a300-2f3e37d55959_terseLabel_en-US" xlink:label="lab_us-gaap_FairValueBalanceSheetGroupingFinancialStatementCaptionsLineItems" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Fair Value, Balance Sheet Grouping, Financial Statement Captions [Line Items]</link:label>
    <link:label id="lab_us-gaap_FairValueBalanceSheetGroupingFinancialStatementCaptionsLineItems_label_en-US" xlink:label="lab_us-gaap_FairValueBalanceSheetGroupingFinancialStatementCaptionsLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Fair Value, Balance Sheet Grouping, Financial Statement Captions [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueBalanceSheetGroupingFinancialStatementCaptionsLineItems" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_FairValueBalanceSheetGroupingFinancialStatementCaptionsLineItems"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FairValueBalanceSheetGroupingFinancialStatementCaptionsLineItems" xlink:to="lab_us-gaap_FairValueBalanceSheetGroupingFinancialStatementCaptionsLineItems" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_GeneralAndAdministrativeExpenseMember_07cbf1ff-4a94-4138-9a45-9dcc9bfad60e_terseLabel_en-US" xlink:label="lab_us-gaap_GeneralAndAdministrativeExpenseMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">General and administrative</link:label>
    <link:label id="lab_us-gaap_GeneralAndAdministrativeExpenseMember_3d100ca1-29c6-4582-b999-42f031db469e_verboseLabel_en-US" xlink:label="lab_us-gaap_GeneralAndAdministrativeExpenseMember" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">General and Administrative Expense</link:label>
    <link:label id="lab_us-gaap_GeneralAndAdministrativeExpenseMember_label_en-US" xlink:label="lab_us-gaap_GeneralAndAdministrativeExpenseMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">General and Administrative Expense [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_GeneralAndAdministrativeExpenseMember" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_GeneralAndAdministrativeExpenseMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_GeneralAndAdministrativeExpenseMember" xlink:to="lab_us-gaap_GeneralAndAdministrativeExpenseMember" xlink:type="arc" order="1"/>
    <link:label id="lab_stpr_SC_412fea15-01bc-41f4-8ecd-63c3d3a94935_terseLabel_en-US" xlink:label="lab_stpr_SC" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">South Carolina</link:label>
    <link:label id="lab_stpr_SC_label_en-US" xlink:label="lab_stpr_SC" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">SOUTH CAROLINA</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_stpr_SC" xlink:href="https://xbrl.sec.gov/stpr/2022/stpr-2022.xsd#stpr_SC"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_stpr_SC" xlink:to="lab_stpr_SC" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_StockIssuedDuringPeriodSharesConversionOfConvertibleSecurities_9d1db464-b994-496f-8087-298b4f25b370_verboseLabel_en-US" xlink:label="lab_us-gaap_StockIssuedDuringPeriodSharesConversionOfConvertibleSecurities" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Conversion of Class B to Class A (in shares)</link:label>
    <link:label id="lab_us-gaap_StockIssuedDuringPeriodSharesConversionOfConvertibleSecurities_label_en-US" xlink:label="lab_us-gaap_StockIssuedDuringPeriodSharesConversionOfConvertibleSecurities" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Stock Issued During Period, Shares, Conversion of Convertible Securities</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_StockIssuedDuringPeriodSharesConversionOfConvertibleSecurities" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_StockIssuedDuringPeriodSharesConversionOfConvertibleSecurities"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_StockIssuedDuringPeriodSharesConversionOfConvertibleSecurities" xlink:to="lab_us-gaap_StockIssuedDuringPeriodSharesConversionOfConvertibleSecurities" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_IncreaseDecreaseInPrepaidReinsurancePremiums_e563d9c5-9466-4275-9674-d93c7001c9b6_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_IncreaseDecreaseInPrepaidReinsurancePremiums" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Prepaid reinsurance premiums</link:label>
    <link:label id="lab_us-gaap_IncreaseDecreaseInPrepaidReinsurancePremiums_label_en-US" xlink:label="lab_us-gaap_IncreaseDecreaseInPrepaidReinsurancePremiums" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Increase (Decrease) in Prepaid Reinsurance Premiums</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncreaseDecreaseInPrepaidReinsurancePremiums" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_IncreaseDecreaseInPrepaidReinsurancePremiums"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IncreaseDecreaseInPrepaidReinsurancePremiums" xlink:to="lab_us-gaap_IncreaseDecreaseInPrepaidReinsurancePremiums" xlink:type="arc" order="1"/>
    <link:label id="lab_root_RootPropertyCasualtyInsuranceCompanyMember_c22ef90f-fd2e-4a8c-bbb0-366bc697911b_terseLabel_en-US" xlink:label="lab_root_RootPropertyCasualtyInsuranceCompanyMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Root Property &amp; Casualty Insurance Company</link:label>
    <link:label id="lab_root_RootPropertyCasualtyInsuranceCompanyMember_label_en-US" xlink:label="lab_root_RootPropertyCasualtyInsuranceCompanyMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Root Property &amp; Casualty Insurance Company [Member]</link:label>
    <link:label id="lab_root_RootPropertyCasualtyInsuranceCompanyMember_documentation_en-US" xlink:label="lab_root_RootPropertyCasualtyInsuranceCompanyMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Root Property &amp; Casualty Insurance Company</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_root_RootPropertyCasualtyInsuranceCompanyMember" xlink:href="root-20220930.xsd#root_RootPropertyCasualtyInsuranceCompanyMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_root_RootPropertyCasualtyInsuranceCompanyMember" xlink:to="lab_root_RootPropertyCasualtyInsuranceCompanyMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CashAndCashEquivalentsMember_d2a4b5e2-ffd3-4636-b230-e13a118dc189_terseLabel_en-US" xlink:label="lab_us-gaap_CashAndCashEquivalentsMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Interest on deposits and cash equivalents</link:label>
    <link:label id="lab_us-gaap_CashAndCashEquivalentsMember_label_en-US" xlink:label="lab_us-gaap_CashAndCashEquivalentsMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Cash and Cash Equivalents [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CashAndCashEquivalentsMember" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_CashAndCashEquivalentsMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CashAndCashEquivalentsMember" xlink:to="lab_us-gaap_CashAndCashEquivalentsMember" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_CoverAbstract_label_en-US" xlink:label="lab_dei_CoverAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Cover [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_CoverAbstract" xlink:href="https://xbrl.sec.gov/dei/2022/dei-2022.xsd#dei_CoverAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_CoverAbstract" xlink:to="lab_dei_CoverAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DebtInstrumentTable_7ad71060-f966-4686-8b51-d816cc7ae78d_terseLabel_en-US" xlink:label="lab_us-gaap_DebtInstrumentTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Schedule of Long-term Debt Instruments [Table]</link:label>
    <link:label id="lab_us-gaap_DebtInstrumentTable_label_en-US" xlink:label="lab_us-gaap_DebtInstrumentTable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Schedule of Long-Term Debt Instruments [Table]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtInstrumentTable" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_DebtInstrumentTable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DebtInstrumentTable" xlink:to="lab_us-gaap_DebtInstrumentTable" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FairValueInputsLevel3Member_1b38374b-ef8f-4158-b430-40622563e129_terseLabel_en-US" xlink:label="lab_us-gaap_FairValueInputsLevel3Member" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Level 3</link:label>
    <link:label id="lab_us-gaap_FairValueInputsLevel3Member_label_en-US" xlink:label="lab_us-gaap_FairValueInputsLevel3Member" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Fair Value, Inputs, Level 3 [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueInputsLevel3Member" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_FairValueInputsLevel3Member"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FairValueInputsLevel3Member" xlink:to="lab_us-gaap_FairValueInputsLevel3Member" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AvailableForSaleSecuritiesDebtSecuritiesNoncurrent_d3dd8542-e764-4ff3-925c-89486d0e7c22_terseLabel_en-US" xlink:label="lab_us-gaap_AvailableForSaleSecuritiesDebtSecuritiesNoncurrent" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Fixed maturities available-for-sale, at fair value (amortized cost: $126.6 and $129.5 at September&#160;30, 2022 and December&#160;31, 2021, respectively)</link:label>
    <link:label id="lab_us-gaap_AvailableForSaleSecuritiesDebtSecuritiesNoncurrent_label_en-US" xlink:label="lab_us-gaap_AvailableForSaleSecuritiesDebtSecuritiesNoncurrent" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt Securities, Available-for-Sale, Noncurrent</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AvailableForSaleSecuritiesDebtSecuritiesNoncurrent" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_AvailableForSaleSecuritiesDebtSecuritiesNoncurrent"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AvailableForSaleSecuritiesDebtSecuritiesNoncurrent" xlink:to="lab_us-gaap_AvailableForSaleSecuritiesDebtSecuritiesNoncurrent" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DisclosureOfCompensationRelatedCostsShareBasedPaymentsTextBlock_78965007-e511-422f-b980-867d093bffa6_terseLabel_en-US" xlink:label="lab_us-gaap_DisclosureOfCompensationRelatedCostsShareBasedPaymentsTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">SHARE-BASED COMPENSATION</link:label>
    <link:label id="lab_us-gaap_DisclosureOfCompensationRelatedCostsShareBasedPaymentsTextBlock_label_en-US" xlink:label="lab_us-gaap_DisclosureOfCompensationRelatedCostsShareBasedPaymentsTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Share-Based Payment Arrangement [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DisclosureOfCompensationRelatedCostsShareBasedPaymentsTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_DisclosureOfCompensationRelatedCostsShareBasedPaymentsTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DisclosureOfCompensationRelatedCostsShareBasedPaymentsTextBlock" xlink:to="lab_us-gaap_DisclosureOfCompensationRelatedCostsShareBasedPaymentsTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_RestructuringAndRelatedActivitiesAbstract_label_en-US" xlink:label="lab_us-gaap_RestructuringAndRelatedActivitiesAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Restructuring and Related Activities [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_RestructuringAndRelatedActivitiesAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_RestructuringAndRelatedActivitiesAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_RestructuringAndRelatedActivitiesAbstract" xlink:to="lab_us-gaap_RestructuringAndRelatedActivitiesAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FixedMaturitiesMember_e3a33308-ecd9-42a2-ba0f-7e30f6d2036e_terseLabel_en-US" xlink:label="lab_us-gaap_FixedMaturitiesMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Total fixed maturities</link:label>
    <link:label id="lab_us-gaap_FixedMaturitiesMember_label_en-US" xlink:label="lab_us-gaap_FixedMaturitiesMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Fixed Maturities [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FixedMaturitiesMember" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_FixedMaturitiesMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FixedMaturitiesMember" xlink:to="lab_us-gaap_FixedMaturitiesMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_OtherAssets_1318cdf0-895b-4584-b05c-dc5ab2ea81c4_terseLabel_en-US" xlink:label="lab_us-gaap_OtherAssets" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Other assets</link:label>
    <link:label id="lab_us-gaap_OtherAssets_label_en-US" xlink:label="lab_us-gaap_OtherAssets" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Other Assets</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OtherAssets" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_OtherAssets"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_OtherAssets" xlink:to="lab_us-gaap_OtherAssets" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_PremiumsWrittenNet_21369682-8f7c-4ced-ac1d-a7ea663df6d0_totalLabel_en-US" xlink:label="lab_us-gaap_PremiumsWrittenNet" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Net premiums written</link:label>
    <link:label id="lab_us-gaap_PremiumsWrittenNet_label_en-US" xlink:label="lab_us-gaap_PremiumsWrittenNet" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Premiums Written, Net</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PremiumsWrittenNet" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_PremiumsWrittenNet"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PremiumsWrittenNet" xlink:to="lab_us-gaap_PremiumsWrittenNet" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsAbstract_c5d8985b-5aa3-4b3f-b58a-87309ffdfec5_terseLabel_en-US" xlink:label="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Net incurred loss and LAE related to:</link:label>
    <link:label id="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsAbstract_3d4eebd2-f319-4306-ac3b-086f2c2181a3_verboseLabel_en-US" xlink:label="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsAbstract" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Losses and LAE incurred:</link:label>
    <link:label id="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsAbstract_label_en-US" xlink:label="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Liability for Unpaid Claims and Claims Adjustment Expense, Incurred Claims [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsAbstract" xlink:to="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_InvestmentTypeCategorizationMember_12cb1349-3e8f-43d8-a9b0-db7278b6e25f_terseLabel_en-US" xlink:label="lab_us-gaap_InvestmentTypeCategorizationMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Investments [Domain]</link:label>
    <link:label id="lab_us-gaap_InvestmentTypeCategorizationMember_label_en-US" xlink:label="lab_us-gaap_InvestmentTypeCategorizationMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Investments [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_InvestmentTypeCategorizationMember" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_InvestmentTypeCategorizationMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_InvestmentTypeCategorizationMember" xlink:to="lab_us-gaap_InvestmentTypeCategorizationMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_PremiumsReceivableAllowanceForDoubtfulAccounts_31a56745-e702-4df6-880e-271674dd7b7f_terseLabel_en-US" xlink:label="lab_us-gaap_PremiumsReceivableAllowanceForDoubtfulAccounts" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Allowance for premiums receivable</link:label>
    <link:label id="lab_us-gaap_PremiumsReceivableAllowanceForDoubtfulAccounts_label_en-US" xlink:label="lab_us-gaap_PremiumsReceivableAllowanceForDoubtfulAccounts" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Premium Receivable, Allowance for Credit Loss</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PremiumsReceivableAllowanceForDoubtfulAccounts" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_PremiumsReceivableAllowanceForDoubtfulAccounts"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PremiumsReceivableAllowanceForDoubtfulAccounts" xlink:to="lab_us-gaap_PremiumsReceivableAllowanceForDoubtfulAccounts" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_ScenarioForecastMember_98611fdf-9f81-4688-8445-7ae64ad5893e_terseLabel_en-US" xlink:label="lab_srt_ScenarioForecastMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Forecast</link:label>
    <link:label id="lab_srt_ScenarioForecastMember_label_en-US" xlink:label="lab_srt_ScenarioForecastMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Forecast [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_ScenarioForecastMember" xlink:href="https://xbrl.fasb.org/srt/2022/elts/srt-2022.xsd#srt_ScenarioForecastMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_ScenarioForecastMember" xlink:to="lab_srt_ScenarioForecastMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LiabilitiesAndStockholdersEquity_81fe54a7-8076-46c2-825b-1e3a2135f124_totalLabel_en-US" xlink:label="lab_us-gaap_LiabilitiesAndStockholdersEquity" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Total liabilities, redeemable convertible preferred stock and stockholders&#8217; equity</link:label>
    <link:label id="lab_us-gaap_LiabilitiesAndStockholdersEquity_label_en-US" xlink:label="lab_us-gaap_LiabilitiesAndStockholdersEquity" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Liabilities and Equity</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LiabilitiesAndStockholdersEquity" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_LiabilitiesAndStockholdersEquity"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LiabilitiesAndStockholdersEquity" xlink:to="lab_us-gaap_LiabilitiesAndStockholdersEquity" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DebtInstrumentTerm_d9a598b5-5572-480d-9dc5-3113a2740115_terseLabel_en-US" xlink:label="lab_us-gaap_DebtInstrumentTerm" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt instrument, term</link:label>
    <link:label id="lab_us-gaap_DebtInstrumentTerm_label_en-US" xlink:label="lab_us-gaap_DebtInstrumentTerm" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt Instrument, Term</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtInstrumentTerm" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_DebtInstrumentTerm"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DebtInstrumentTerm" xlink:to="lab_us-gaap_DebtInstrumentTerm" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidCurrentYear1_2ee9a587-8f82-4c6e-9788-6ef54bb5633d_terseLabel_en-US" xlink:label="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidCurrentYear1" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Current year</link:label>
    <link:label id="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidCurrentYear1_label_en-US" xlink:label="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidCurrentYear1" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Liability for Unpaid Claims and Claims Adjustment Expense, Claims Paid, Current Year</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidCurrentYear1" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidCurrentYear1"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidCurrentYear1" xlink:to="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidCurrentYear1" xlink:type="arc" order="1"/>
    <link:label id="lab_stpr_PA_7c039ded-e89f-485b-9aca-fb40bcb57e87_terseLabel_en-US" xlink:label="lab_stpr_PA" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Pennsylvania</link:label>
    <link:label id="lab_stpr_PA_label_en-US" xlink:label="lab_stpr_PA" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">PENNSYLVANIA</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_stpr_PA" xlink:href="https://xbrl.sec.gov/stpr/2022/stpr-2022.xsd#stpr_PA"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_stpr_PA" xlink:to="lab_stpr_PA" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LongtermDebtTypeAxis_d0368720-db55-47ef-91df-1f0d66402f5e_terseLabel_en-US" xlink:label="lab_us-gaap_LongtermDebtTypeAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Long-term Debt, Type [Axis]</link:label>
    <link:label id="lab_us-gaap_LongtermDebtTypeAxis_label_en-US" xlink:label="lab_us-gaap_LongtermDebtTypeAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Long-Term Debt, Type [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LongtermDebtTypeAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_LongtermDebtTypeAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LongtermDebtTypeAxis" xlink:to="lab_us-gaap_LongtermDebtTypeAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_root_StandardPoorsAPlusAAMinusRatingMember_fbab021a-7a48-4985-bc90-1cb6ea2af01a_terseLabel_en-US" xlink:label="lab_root_StandardPoorsAPlusAAMinusRatingMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">A+, A, A-</link:label>
    <link:label id="lab_root_StandardPoorsAPlusAAMinusRatingMember_label_en-US" xlink:label="lab_root_StandardPoorsAPlusAAMinusRatingMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Standard &amp; Poor's, A Plus, A, A Minus Rating [Member]</link:label>
    <link:label id="lab_root_StandardPoorsAPlusAAMinusRatingMember_documentation_en-US" xlink:label="lab_root_StandardPoorsAPlusAAMinusRatingMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Standard &amp; Poor's, A Plus, A, A Minus Rating</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_root_StandardPoorsAPlusAAMinusRatingMember" xlink:href="root-20220930.xsd#root_StandardPoorsAPlusAAMinusRatingMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_root_StandardPoorsAPlusAAMinusRatingMember" xlink:to="lab_root_StandardPoorsAPlusAAMinusRatingMember" xlink:type="arc" order="1"/>
    <link:label id="lab_root_FairValueOfWarrantsPercentage_09b8b669-5e0c-4643-8a72-c4a652b5b526_terseLabel_en-US" xlink:label="lab_root_FairValueOfWarrantsPercentage" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Fair value of warrants percentage (in percent)</link:label>
    <link:label id="lab_root_FairValueOfWarrantsPercentage_label_en-US" xlink:label="lab_root_FairValueOfWarrantsPercentage" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Fair Value Of Warrants Percentage</link:label>
    <link:label id="lab_root_FairValueOfWarrantsPercentage_documentation_en-US" xlink:label="lab_root_FairValueOfWarrantsPercentage" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Fair Value Of Warrants Percentage</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_root_FairValueOfWarrantsPercentage" xlink:href="root-20220930.xsd#root_FairValueOfWarrantsPercentage"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_root_FairValueOfWarrantsPercentage" xlink:to="lab_root_FairValueOfWarrantsPercentage" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_OrganizationConsolidationAndPresentationOfFinancialStatementsAbstract_label_en-US" xlink:label="lab_us-gaap_OrganizationConsolidationAndPresentationOfFinancialStatementsAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Organization, Consolidation and Presentation of Financial Statements [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OrganizationConsolidationAndPresentationOfFinancialStatementsAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_OrganizationConsolidationAndPresentationOfFinancialStatementsAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_OrganizationConsolidationAndPresentationOfFinancialStatementsAbstract" xlink:to="lab_us-gaap_OrganizationConsolidationAndPresentationOfFinancialStatementsAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AOCIAttributableToParentNetOfTaxRollForward_88c597fa-9674-460f-b0a8-46a29439e611_terseLabel_en-US" xlink:label="lab_us-gaap_AOCIAttributableToParentNetOfTaxRollForward" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">AOCI Attributable to Parent, Net of Tax [Roll Forward]</link:label>
    <link:label id="lab_us-gaap_AOCIAttributableToParentNetOfTaxRollForward_label_en-US" xlink:label="lab_us-gaap_AOCIAttributableToParentNetOfTaxRollForward" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">AOCI Attributable to Parent, Net of Tax [Roll Forward]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AOCIAttributableToParentNetOfTaxRollForward" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_AOCIAttributableToParentNetOfTaxRollForward"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AOCIAttributableToParentNetOfTaxRollForward" xlink:to="lab_us-gaap_AOCIAttributableToParentNetOfTaxRollForward" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EmployeeServiceShareBasedCompensationAllocationOfRecognizedPeriodCostsLineItems_227ecf5f-8995-412b-a096-48a8e61b2574_terseLabel_en-US" xlink:label="lab_us-gaap_EmployeeServiceShareBasedCompensationAllocationOfRecognizedPeriodCostsLineItems" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Share-based Payment Arrangement, Expensed and Capitalized, Amount [Line Items]</link:label>
    <link:label id="lab_us-gaap_EmployeeServiceShareBasedCompensationAllocationOfRecognizedPeriodCostsLineItems_label_en-US" xlink:label="lab_us-gaap_EmployeeServiceShareBasedCompensationAllocationOfRecognizedPeriodCostsLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Share-Based Payment Arrangement, Expensed and Capitalized, Amount [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EmployeeServiceShareBasedCompensationAllocationOfRecognizedPeriodCostsLineItems" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_EmployeeServiceShareBasedCompensationAllocationOfRecognizedPeriodCostsLineItems"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EmployeeServiceShareBasedCompensationAllocationOfRecognizedPeriodCostsLineItems" xlink:to="lab_us-gaap_EmployeeServiceShareBasedCompensationAllocationOfRecognizedPeriodCostsLineItems" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FairValueInputsLevel2Member_e3882439-0ffb-495a-8419-a5bcf6638434_terseLabel_en-US" xlink:label="lab_us-gaap_FairValueInputsLevel2Member" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Level 2</link:label>
    <link:label id="lab_us-gaap_FairValueInputsLevel2Member_label_en-US" xlink:label="lab_us-gaap_FairValueInputsLevel2Member" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Fair Value, Inputs, Level 2 [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueInputsLevel2Member" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_FairValueInputsLevel2Member"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FairValueInputsLevel2Member" xlink:to="lab_us-gaap_FairValueInputsLevel2Member" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_CurrentFiscalYearEndDate_75136ae0-c718-4aee-a73c-65e0a05143e4_terseLabel_en-US" xlink:label="lab_dei_CurrentFiscalYearEndDate" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Current Fiscal Year End Date</link:label>
    <link:label id="lab_dei_CurrentFiscalYearEndDate_label_en-US" xlink:label="lab_dei_CurrentFiscalYearEndDate" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Current Fiscal Year End Date</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_CurrentFiscalYearEndDate" xlink:href="https://xbrl.sec.gov/dei/2022/dei-2022.xsd#dei_CurrentFiscalYearEndDate"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_CurrentFiscalYearEndDate" xlink:to="lab_dei_CurrentFiscalYearEndDate" xlink:type="arc" order="1"/>
    <link:label id="lab_stpr_OK_e5cca72a-bbe6-4743-a18a-4cdb581aacc0_terseLabel_en-US" xlink:label="lab_stpr_OK" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Oklahoma</link:label>
    <link:label id="lab_stpr_OK_label_en-US" xlink:label="lab_stpr_OK" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">OKLAHOMA</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_stpr_OK" xlink:href="https://xbrl.sec.gov/stpr/2022/stpr-2022.xsd#stpr_OK"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_stpr_OK" xlink:to="lab_stpr_OK" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesSingleMaturityDateAmortizedCostBasisAbstract_9758d966-a244-416a-8024-f24c22babe27_terseLabel_en-US" xlink:label="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesSingleMaturityDateAmortizedCostBasisAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Amortized Cost</link:label>
    <link:label id="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesSingleMaturityDateAmortizedCostBasisAbstract_label_en-US" xlink:label="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesSingleMaturityDateAmortizedCostBasisAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt Securities, Available-for-Sale, Maturity, Allocated and Single Maturity Date, Amortized Cost [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesSingleMaturityDateAmortizedCostBasisAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_AvailableForSaleSecuritiesDebtMaturitiesSingleMaturityDateAmortizedCostBasisAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesSingleMaturityDateAmortizedCostBasisAbstract" xlink:to="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesSingleMaturityDateAmortizedCostBasisAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleRealizedGain_142039ef-db03-4901-87c4-7d3c2f5c81ba_terseLabel_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleRealizedGain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Realized gains on investments</link:label>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleRealizedGain_label_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleRealizedGain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt Securities, Available-for-Sale, Realized Gain</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtSecuritiesAvailableForSaleRealizedGain" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_DebtSecuritiesAvailableForSaleRealizedGain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DebtSecuritiesAvailableForSaleRealizedGain" xlink:to="lab_us-gaap_DebtSecuritiesAvailableForSaleRealizedGain" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_VestingAxis_ad84674e-05fd-4c3d-8f5f-108710d6990d_terseLabel_en-US" xlink:label="lab_us-gaap_VestingAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Vesting [Axis]</link:label>
    <link:label id="lab_us-gaap_VestingAxis_label_en-US" xlink:label="lab_us-gaap_VestingAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Vesting [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_VestingAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_VestingAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_VestingAxis" xlink:to="lab_us-gaap_VestingAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EarningsPerShareDiluted_5bdbab96-949c-404b-9042-71d9377115e5_terseLabel_en-US" xlink:label="lab_us-gaap_EarningsPerShareDiluted" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Loss per common share: diluted (both Class A and B) (in dollars per share)</link:label>
    <link:label id="lab_us-gaap_EarningsPerShareDiluted_label_en-US" xlink:label="lab_us-gaap_EarningsPerShareDiluted" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Earnings Per Share, Diluted</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EarningsPerShareDiluted" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_EarningsPerShareDiluted"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EarningsPerShareDiluted" xlink:to="lab_us-gaap_EarningsPerShareDiluted" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ShareBasedCompensationAwardTrancheTwoMember_e1f55c62-c1ad-4d8c-be48-a7ac7a3cdbeb_terseLabel_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationAwardTrancheTwoMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Tranche 2</link:label>
    <link:label id="lab_us-gaap_ShareBasedCompensationAwardTrancheTwoMember_label_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationAwardTrancheTwoMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Share-Based Payment Arrangement, Tranche Two [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShareBasedCompensationAwardTrancheTwoMember" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ShareBasedCompensationAwardTrancheTwoMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ShareBasedCompensationAwardTrancheTwoMember" xlink:to="lab_us-gaap_ShareBasedCompensationAwardTrancheTwoMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_StockholdersEquityNoteStockSplitConversionRatio1_f8c54dfd-480d-4682-815e-e211e6980da5_terseLabel_en-US" xlink:label="lab_us-gaap_StockholdersEquityNoteStockSplitConversionRatio1" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Conversion ratio</link:label>
    <link:label id="lab_us-gaap_StockholdersEquityNoteStockSplitConversionRatio1_label_en-US" xlink:label="lab_us-gaap_StockholdersEquityNoteStockSplitConversionRatio1" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Stockholders' Equity Note, Stock Split, Conversion Ratio</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_StockholdersEquityNoteStockSplitConversionRatio1" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_StockholdersEquityNoteStockSplitConversionRatio1"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_StockholdersEquityNoteStockSplitConversionRatio1" xlink:to="lab_us-gaap_StockholdersEquityNoteStockSplitConversionRatio1" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleAmortizedCostNoncurrent_06c0303d-ff1c-4329-8719-a25c1f5dab6b_verboseLabel_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleAmortizedCostNoncurrent" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Amortized cost, fixed maturities</link:label>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleAmortizedCostNoncurrent_label_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleAmortizedCostNoncurrent" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt Securities, Available-for-Sale, Amortized Cost, Noncurrent</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtSecuritiesAvailableForSaleAmortizedCostNoncurrent" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_DebtSecuritiesAvailableForSaleAmortizedCostNoncurrent"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DebtSecuritiesAvailableForSaleAmortizedCostNoncurrent" xlink:to="lab_us-gaap_DebtSecuritiesAvailableForSaleAmortizedCostNoncurrent" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_PaymentsOfStockIssuanceCosts_2fe2ccc4-af77-4c41-912b-c6389b436a14_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_PaymentsOfStockIssuanceCosts" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Payment of preferred stock and related warrants issuance costs</link:label>
    <link:label id="lab_us-gaap_PaymentsOfStockIssuanceCosts_label_en-US" xlink:label="lab_us-gaap_PaymentsOfStockIssuanceCosts" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Payments of Stock Issuance Costs</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PaymentsOfStockIssuanceCosts" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_PaymentsOfStockIssuanceCosts"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PaymentsOfStockIssuanceCosts" xlink:to="lab_us-gaap_PaymentsOfStockIssuanceCosts" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AdjustmentsToAdditionalPaidInCapitalSharebasedCompensationRequisiteServicePeriodRecognitionValue_cc60caa1-c875-4cf2-b578-91a10c8902f0_terseLabel_en-US" xlink:label="lab_us-gaap_AdjustmentsToAdditionalPaidInCapitalSharebasedCompensationRequisiteServicePeriodRecognitionValue" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Common stock&#8212;share-based compensation expense</link:label>
    <link:label id="lab_us-gaap_AdjustmentsToAdditionalPaidInCapitalSharebasedCompensationRequisiteServicePeriodRecognitionValue_label_en-US" xlink:label="lab_us-gaap_AdjustmentsToAdditionalPaidInCapitalSharebasedCompensationRequisiteServicePeriodRecognitionValue" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">APIC, Share-Based Payment Arrangement, Increase for Cost Recognition</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AdjustmentsToAdditionalPaidInCapitalSharebasedCompensationRequisiteServicePeriodRecognitionValue" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_AdjustmentsToAdditionalPaidInCapitalSharebasedCompensationRequisiteServicePeriodRecognitionValue"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AdjustmentsToAdditionalPaidInCapitalSharebasedCompensationRequisiteServicePeriodRecognitionValue" xlink:to="lab_us-gaap_AdjustmentsToAdditionalPaidInCapitalSharebasedCompensationRequisiteServicePeriodRecognitionValue" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ConcentrationRiskByTypeAxis_ae38e908-8158-46ab-9e32-11f237a86c0f_terseLabel_en-US" xlink:label="lab_us-gaap_ConcentrationRiskByTypeAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Concentration Risk Type [Axis]</link:label>
    <link:label id="lab_us-gaap_ConcentrationRiskByTypeAxis_label_en-US" xlink:label="lab_us-gaap_ConcentrationRiskByTypeAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Concentration Risk Type [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ConcentrationRiskByTypeAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ConcentrationRiskByTypeAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ConcentrationRiskByTypeAxis" xlink:to="lab_us-gaap_ConcentrationRiskByTypeAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterTenYearsFairValue_6b898d04-db25-4c9e-af46-75a52b6bfed2_terseLabel_en-US" xlink:label="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterTenYearsFairValue" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Due after 10 years</link:label>
    <link:label id="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterTenYearsFairValue_label_en-US" xlink:label="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterTenYearsFairValue" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt Securities, Available-for-Sale, Fair Value, Maturity, Allocated and Single Maturity Date, after Year 10</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterTenYearsFairValue" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterTenYearsFairValue"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterTenYearsFairValue" xlink:to="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterTenYearsFairValue" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseNet_d1aedb3a-ae8a-411b-8fba-f15857bff3c1_totalLabel_en-US" xlink:label="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseNet" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Net loss and LAE reserves, January 1</link:label>
    <link:label id="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseNet_1099732a-7ccf-482a-8fcf-892320334028_periodEndLabel_en-US" xlink:label="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseNet" xlink:role="http://www.xbrl.org/2003/role/periodEndLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Net loss and LAE reserves, September 30</link:label>
    <link:label id="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseNet_label_en-US" xlink:label="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseNet" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Liability for Unpaid Claims and Claims Adjustment Expense, Net</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseNet" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseNet"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseNet" xlink:to="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseNet" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_RestructuringCostAndReserveLineItems_f9be4edb-aefd-4288-91f2-13be4ce8f178_terseLabel_en-US" xlink:label="lab_us-gaap_RestructuringCostAndReserveLineItems" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Restructuring Cost and Reserve [Line Items]</link:label>
    <link:label id="lab_us-gaap_RestructuringCostAndReserveLineItems_label_en-US" xlink:label="lab_us-gaap_RestructuringCostAndReserveLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Restructuring Cost and Reserve [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_RestructuringCostAndReserveLineItems" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_RestructuringCostAndReserveLineItems"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_RestructuringCostAndReserveLineItems" xlink:to="lab_us-gaap_RestructuringCostAndReserveLineItems" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_PaymentsToDevelopSoftware_d360b40a-46c8-4dc6-b95e-d90416e21218_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_PaymentsToDevelopSoftware" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Capitalization of internally developed software</link:label>
    <link:label id="lab_us-gaap_PaymentsToDevelopSoftware_label_en-US" xlink:label="lab_us-gaap_PaymentsToDevelopSoftware" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Payments to Develop Software</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PaymentsToDevelopSoftware" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_PaymentsToDevelopSoftware"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PaymentsToDevelopSoftware" xlink:to="lab_us-gaap_PaymentsToDevelopSoftware" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CorporateDebtSecuritiesMember_0f6c13d0-1c66-4b5e-8e2f-fde5a2d55b0d_terseLabel_en-US" xlink:label="lab_us-gaap_CorporateDebtSecuritiesMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Corporate debt securities</link:label>
    <link:label id="lab_us-gaap_CorporateDebtSecuritiesMember_label_en-US" xlink:label="lab_us-gaap_CorporateDebtSecuritiesMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Corporate Debt Securities [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CorporateDebtSecuritiesMember" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_CorporateDebtSecuritiesMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CorporateDebtSecuritiesMember" xlink:to="lab_us-gaap_CorporateDebtSecuritiesMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_InvestmentIncomeInvestmentExpense_54530f61-8c00-45d1-8821-d5c19a025cea_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_InvestmentIncomeInvestmentExpense" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Investment expense</link:label>
    <link:label id="lab_us-gaap_InvestmentIncomeInvestmentExpense_label_en-US" xlink:label="lab_us-gaap_InvestmentIncomeInvestmentExpense" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Investment Income, Investment Expense</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_InvestmentIncomeInvestmentExpense" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_InvestmentIncomeInvestmentExpense"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_InvestmentIncomeInvestmentExpense" xlink:to="lab_us-gaap_InvestmentIncomeInvestmentExpense" xlink:type="arc" order="1"/>
    <link:label id="lab_root_StandardPoorsBBBPlusBBBBBBMinusRatingMember_065ccb7a-6d43-454c-9166-e7df5704eeba_terseLabel_en-US" xlink:label="lab_root_StandardPoorsBBBPlusBBBBBBMinusRatingMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">BBB+, BBB, BBB-</link:label>
    <link:label id="lab_root_StandardPoorsBBBPlusBBBBBBMinusRatingMember_label_en-US" xlink:label="lab_root_StandardPoorsBBBPlusBBBBBBMinusRatingMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Standard &amp; Poor's, BBB Plus, BBB, BBB Minus Rating [Member]</link:label>
    <link:label id="lab_root_StandardPoorsBBBPlusBBBBBBMinusRatingMember_documentation_en-US" xlink:label="lab_root_StandardPoorsBBBPlusBBBBBBMinusRatingMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Standard &amp; Poor's, BBB Plus, BBB, BBB Minus Rating</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_root_StandardPoorsBBBPlusBBBBBBMinusRatingMember" xlink:href="root-20220930.xsd#root_StandardPoorsBBBPlusBBBBBBMinusRatingMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_root_StandardPoorsBBBPlusBBBBBBMinusRatingMember" xlink:to="lab_root_StandardPoorsBBBPlusBBBBBBMinusRatingMember" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_EntityAddressAddressLine2_39a33ee1-ca35-4e7a-9fe6-cc80a3af5ecf_terseLabel_en-US" xlink:label="lab_dei_EntityAddressAddressLine2" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Entity Address, Address Line Two</link:label>
    <link:label id="lab_dei_EntityAddressAddressLine2_label_en-US" xlink:label="lab_dei_EntityAddressAddressLine2" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Entity Address, Address Line Two</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_EntityAddressAddressLine2" xlink:href="https://xbrl.sec.gov/dei/2022/dei-2022.xsd#dei_EntityAddressAddressLine2"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_EntityAddressAddressLine2" xlink:to="lab_dei_EntityAddressAddressLine2" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_EntityAddressAddressLine1_c31ca6cb-c3eb-4009-8c74-b6f90ebe4b2e_terseLabel_en-US" xlink:label="lab_dei_EntityAddressAddressLine1" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Entity Address, Address Line One</link:label>
    <link:label id="lab_dei_EntityAddressAddressLine1_label_en-US" xlink:label="lab_dei_EntityAddressAddressLine1" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Entity Address, Address Line One</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_EntityAddressAddressLine1" xlink:href="https://xbrl.sec.gov/dei/2022/dei-2022.xsd#dei_EntityAddressAddressLine1"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_EntityAddressAddressLine1" xlink:to="lab_dei_EntityAddressAddressLine1" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ReinsuranceTextBlock_2fb26d97-689e-4cf6-b9ef-1b37bf494a88_verboseLabel_en-US" xlink:label="lab_us-gaap_ReinsuranceTextBlock" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">REINSURANCE</link:label>
    <link:label id="lab_us-gaap_ReinsuranceTextBlock_ec1d35d0-827b-4280-90f7-47bb39b639f6_terseLabel_en-US" xlink:label="lab_us-gaap_ReinsuranceTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">GEOGRAPHICAL BREAKDOWN OF GROSS WRITTEN PREMIUM</link:label>
    <link:label id="lab_us-gaap_ReinsuranceTextBlock_label_en-US" xlink:label="lab_us-gaap_ReinsuranceTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Reinsurance [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ReinsuranceTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ReinsuranceTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ReinsuranceTextBlock" xlink:to="lab_us-gaap_ReinsuranceTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ClassOfStockDomain_0a456e5e-ee9a-427c-a1f8-bdeafccfe8bd_terseLabel_en-US" xlink:label="lab_us-gaap_ClassOfStockDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Class of Stock [Domain]</link:label>
    <link:label id="lab_us-gaap_ClassOfStockDomain_label_en-US" xlink:label="lab_us-gaap_ClassOfStockDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Class of Stock [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ClassOfStockDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ClassOfStockDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ClassOfStockDomain" xlink:to="lab_us-gaap_ClassOfStockDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CededPremiumsWritten_121e5039-6e91-4e4b-b218-0fdd93e60036_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_CededPremiumsWritten" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Ceded</link:label>
    <link:label id="lab_us-gaap_CededPremiumsWritten_label_en-US" xlink:label="lab_us-gaap_CededPremiumsWritten" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Ceded Premiums Written</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CededPremiumsWritten" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_CededPremiumsWritten"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CededPremiumsWritten" xlink:to="lab_us-gaap_CededPremiumsWritten" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FairValueDisclosuresAbstract_label_en-US" xlink:label="lab_us-gaap_FairValueDisclosuresAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Fair Value Disclosures [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueDisclosuresAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_FairValueDisclosuresAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FairValueDisclosuresAbstract" xlink:to="lab_us-gaap_FairValueDisclosuresAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_InterestExpense_78bfe306-dba7-4350-b79c-ff07a367113b_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_InterestExpense" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Interest expense</link:label>
    <link:label id="lab_us-gaap_InterestExpense_label_en-US" xlink:label="lab_us-gaap_InterestExpense" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Interest Expense</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_InterestExpense" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_InterestExpense"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_InterestExpense" xlink:to="lab_us-gaap_InterestExpense" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaims1_f59fc907-5e98-4369-8da5-7866496b0128_verboseLabel_en-US" xlink:label="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaims1" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Loss and loss adjustment expenses</link:label>
    <link:label id="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaims1_4e1c4a99-dab4-432e-9578-26f55f84a35e_terseLabel_en-US" xlink:label="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaims1" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Total incurred</link:label>
    <link:label id="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaims1_b7b38f54-ddbd-4af9-8114-f5648974d5ad_totalLabel_en-US" xlink:label="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaims1" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Total incurred</link:label>
    <link:label id="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaims1_label_en-US" xlink:label="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaims1" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Liability for Unpaid Claims and Claims Adjustment Expense, Incurred Claims</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaims1" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaims1"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaims1" xlink:to="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaims1" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_OtherComprehensiveIncomeUnrealizedHoldingGainLossOnSecuritiesArisingDuringPeriodNetOfTax_11e70fff-de52-4db2-9db6-c71aebcf75da_terseLabel_en-US" xlink:label="lab_us-gaap_OtherComprehensiveIncomeUnrealizedHoldingGainLossOnSecuritiesArisingDuringPeriodNetOfTax" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Changes in net unrealized losses on investments</link:label>
    <link:label id="lab_us-gaap_OtherComprehensiveIncomeUnrealizedHoldingGainLossOnSecuritiesArisingDuringPeriodNetOfTax_label_en-US" xlink:label="lab_us-gaap_OtherComprehensiveIncomeUnrealizedHoldingGainLossOnSecuritiesArisingDuringPeriodNetOfTax" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">OCI, Debt Securities, Available-for-Sale, Unrealized Holding Gain (Loss), before Adjustment, after Tax</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OtherComprehensiveIncomeUnrealizedHoldingGainLossOnSecuritiesArisingDuringPeriodNetOfTax" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_OtherComprehensiveIncomeUnrealizedHoldingGainLossOnSecuritiesArisingDuringPeriodNetOfTax"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_OtherComprehensiveIncomeUnrealizedHoldingGainLossOnSecuritiesArisingDuringPeriodNetOfTax" xlink:to="lab_us-gaap_OtherComprehensiveIncomeUnrealizedHoldingGainLossOnSecuritiesArisingDuringPeriodNetOfTax" xlink:type="arc" order="1"/>
    <link:label id="lab_root_DebtSecuritiesAvailableForSaleCurrentMember_db8364c6-e2d2-4711-894c-c7917b9b207b_terseLabel_en-US" xlink:label="lab_root_DebtSecuritiesAvailableForSaleCurrentMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Short-term investments</link:label>
    <link:label id="lab_root_DebtSecuritiesAvailableForSaleCurrentMember_label_en-US" xlink:label="lab_root_DebtSecuritiesAvailableForSaleCurrentMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt Securities Available For Sale Current [Member]</link:label>
    <link:label id="lab_root_DebtSecuritiesAvailableForSaleCurrentMember_documentation_en-US" xlink:label="lab_root_DebtSecuritiesAvailableForSaleCurrentMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt Securities Available For Sale Current</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_root_DebtSecuritiesAvailableForSaleCurrentMember" xlink:href="root-20220930.xsd#root_DebtSecuritiesAvailableForSaleCurrentMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_root_DebtSecuritiesAvailableForSaleCurrentMember" xlink:to="lab_root_DebtSecuritiesAvailableForSaleCurrentMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_GrossInvestmentIncomeOperating_03f6997e-cf6b-40c5-8699-9fcddcccf093_terseLabel_en-US" xlink:label="lab_us-gaap_GrossInvestmentIncomeOperating" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Realized gain value</link:label>
    <link:label id="lab_us-gaap_GrossInvestmentIncomeOperating_label_en-US" xlink:label="lab_us-gaap_GrossInvestmentIncomeOperating" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Gross Investment Income, Operating</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_GrossInvestmentIncomeOperating" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_GrossInvestmentIncomeOperating"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_GrossInvestmentIncomeOperating" xlink:to="lab_us-gaap_GrossInvestmentIncomeOperating" xlink:type="arc" order="1"/>
    <link:label id="lab_stpr_UT_19a679d3-ff57-4853-a177-f7dc024b040e_terseLabel_en-US" xlink:label="lab_stpr_UT" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Utah</link:label>
    <link:label id="lab_stpr_UT_label_en-US" xlink:label="lab_stpr_UT" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">UTAH</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_stpr_UT" xlink:href="https://xbrl.sec.gov/stpr/2022/stpr-2022.xsd#stpr_UT"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_stpr_UT" xlink:to="lab_stpr_UT" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ScheduleOfDebtInstrumentsTextBlock_f87a1456-1127-4d89-b31a-a14ed7b2fe77_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfDebtInstrumentsTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Schedule of Long Term Debt</link:label>
    <link:label id="lab_us-gaap_ScheduleOfDebtInstrumentsTextBlock_label_en-US" xlink:label="lab_us-gaap_ScheduleOfDebtInstrumentsTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Schedule of Long-Term Debt Instruments [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfDebtInstrumentsTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ScheduleOfDebtInstrumentsTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ScheduleOfDebtInstrumentsTextBlock" xlink:to="lab_us-gaap_ScheduleOfDebtInstrumentsTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EquityAbstract_label_en-US" xlink:label="lab_us-gaap_EquityAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Equity [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EquityAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_EquityAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EquityAbstract" xlink:to="lab_us-gaap_EquityAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_SubsequentEventTable_a828d6f4-92b2-4cf8-a0fd-4c3be7f6d971_terseLabel_en-US" xlink:label="lab_us-gaap_SubsequentEventTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Subsequent Event [Table]</link:label>
    <link:label id="lab_us-gaap_SubsequentEventTable_label_en-US" xlink:label="lab_us-gaap_SubsequentEventTable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Subsequent Event [Table]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SubsequentEventTable" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_SubsequentEventTable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_SubsequentEventTable" xlink:to="lab_us-gaap_SubsequentEventTable" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsVestedInPeriod_ca8430b9-49c3-4a24-8f0f-0cb9f33f62ee_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsVestedInPeriod" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Vested (in shares)</link:label>
    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsVestedInPeriod_label_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsVestedInPeriod" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Share-Based Compensation Arrangement by Share-Based Payment Award, Equity Instruments Other than Options, Vested in Period</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsVestedInPeriod" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsVestedInPeriod"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsVestedInPeriod" xlink:to="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsVestedInPeriod" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_EntityTaxIdentificationNumber_075fb982-8546-4f35-b4a8-2a460376b921_terseLabel_en-US" xlink:label="lab_dei_EntityTaxIdentificationNumber" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Entity Tax Identification Number</link:label>
    <link:label id="lab_dei_EntityTaxIdentificationNumber_label_en-US" xlink:label="lab_dei_EntityTaxIdentificationNumber" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Entity Tax Identification Number</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_EntityTaxIdentificationNumber" xlink:href="https://xbrl.sec.gov/dei/2022/dei-2022.xsd#dei_EntityTaxIdentificationNumber"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_EntityTaxIdentificationNumber" xlink:to="lab_dei_EntityTaxIdentificationNumber" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_SharebasedCompensationArrangementBySharebasedPaymentAwardEquityInstrumentsOtherThanOptionsAggregateIntrinsicValueAbstract_a41c6ed1-3def-4e3c-bbd5-05352cbce4d1_terseLabel_en-US" xlink:label="lab_us-gaap_SharebasedCompensationArrangementBySharebasedPaymentAwardEquityInstrumentsOtherThanOptionsAggregateIntrinsicValueAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Aggregate Intrinsic Value</link:label>
    <link:label id="lab_us-gaap_SharebasedCompensationArrangementBySharebasedPaymentAwardEquityInstrumentsOtherThanOptionsAggregateIntrinsicValueAbstract_label_en-US" xlink:label="lab_us-gaap_SharebasedCompensationArrangementBySharebasedPaymentAwardEquityInstrumentsOtherThanOptionsAggregateIntrinsicValueAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Share-Based Compensation Arrangement by Share-Based Payment Award, Equity Instruments Other than Options, Aggregate Intrinsic Value [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SharebasedCompensationArrangementBySharebasedPaymentAwardEquityInstrumentsOtherThanOptionsAggregateIntrinsicValueAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_SharebasedCompensationArrangementBySharebasedPaymentAwardEquityInstrumentsOtherThanOptionsAggregateIntrinsicValueAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_SharebasedCompensationArrangementBySharebasedPaymentAwardEquityInstrumentsOtherThanOptionsAggregateIntrinsicValueAbstract" xlink:to="lab_us-gaap_SharebasedCompensationArrangementBySharebasedPaymentAwardEquityInstrumentsOtherThanOptionsAggregateIntrinsicValueAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_IncreaseDecreaseInPremiumsReceivable_33d1c66b-ce98-4e92-bd4b-62ad34abb4e9_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_IncreaseDecreaseInPremiumsReceivable" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Premiums receivable</link:label>
    <link:label id="lab_us-gaap_IncreaseDecreaseInPremiumsReceivable_label_en-US" xlink:label="lab_us-gaap_IncreaseDecreaseInPremiumsReceivable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Increase (Decrease) in Premiums Receivable</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncreaseDecreaseInPremiumsReceivable" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_IncreaseDecreaseInPremiumsReceivable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IncreaseDecreaseInPremiumsReceivable" xlink:to="lab_us-gaap_IncreaseDecreaseInPremiumsReceivable" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_IncreaseDecreaseInReinsurancePayables_b444c6f4-b8d2-481f-8335-ecf9b9402ed8_terseLabel_en-US" xlink:label="lab_us-gaap_IncreaseDecreaseInReinsurancePayables" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Reinsurance premiums payable</link:label>
    <link:label id="lab_us-gaap_IncreaseDecreaseInReinsurancePayables_label_en-US" xlink:label="lab_us-gaap_IncreaseDecreaseInReinsurancePayables" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Increase (Decrease) in Reinsurance Payables</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncreaseDecreaseInReinsurancePayables" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_IncreaseDecreaseInReinsurancePayables"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IncreaseDecreaseInReinsurancePayables" xlink:to="lab_us-gaap_IncreaseDecreaseInReinsurancePayables" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalentsPeriodIncreaseDecreaseIncludingExchangeRateEffect_11fce848-2841-4c3e-be7a-3d999c142f3b_totalLabel_en-US" xlink:label="lab_us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalentsPeriodIncreaseDecreaseIncludingExchangeRateEffect" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Net increase (decrease) in cash, cash equivalents and restricted cash</link:label>
    <link:label id="lab_us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalentsPeriodIncreaseDecreaseIncludingExchangeRateEffect_label_en-US" xlink:label="lab_us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalentsPeriodIncreaseDecreaseIncludingExchangeRateEffect" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Cash, Cash Equivalents, Restricted Cash, and Restricted Cash Equivalents, Period Increase (Decrease), Including Exchange Rate Effect</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalentsPeriodIncreaseDecreaseIncludingExchangeRateEffect" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalentsPeriodIncreaseDecreaseIncludingExchangeRateEffect"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalentsPeriodIncreaseDecreaseIncludingExchangeRateEffect" xlink:to="lab_us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalentsPeriodIncreaseDecreaseIncludingExchangeRateEffect" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_WarrantsNotSettleableInCashFairValueDisclosure_b1fb3c69-e9dc-4778-86d6-04d6e9c47ebc_terseLabel_en-US" xlink:label="lab_us-gaap_WarrantsNotSettleableInCashFairValueDisclosure" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Fair value of warrants</link:label>
    <link:label id="lab_us-gaap_WarrantsNotSettleableInCashFairValueDisclosure_label_en-US" xlink:label="lab_us-gaap_WarrantsNotSettleableInCashFairValueDisclosure" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Warrants Not Settleable in Cash, Fair Value Disclosure</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_WarrantsNotSettleableInCashFairValueDisclosure" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_WarrantsNotSettleableInCashFairValueDisclosure"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_WarrantsNotSettleableInCashFairValueDisclosure" xlink:to="lab_us-gaap_WarrantsNotSettleableInCashFairValueDisclosure" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ScheduleOfRestructuringAndRelatedCostsTextBlock_4dc883ac-a911-46ff-970f-c5ad9123de58_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfRestructuringAndRelatedCostsTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Restructuring Costs</link:label>
    <link:label id="lab_us-gaap_ScheduleOfRestructuringAndRelatedCostsTextBlock_label_en-US" xlink:label="lab_us-gaap_ScheduleOfRestructuringAndRelatedCostsTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Restructuring and Related Costs [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfRestructuringAndRelatedCostsTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ScheduleOfRestructuringAndRelatedCostsTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ScheduleOfRestructuringAndRelatedCostsTextBlock" xlink:to="lab_us-gaap_ScheduleOfRestructuringAndRelatedCostsTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_EntityCentralIndexKey_41483bf8-e6b0-4331-8eef-b8adc8a1ae3b_terseLabel_en-US" xlink:label="lab_dei_EntityCentralIndexKey" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Entity Central Index Key</link:label>
    <link:label id="lab_dei_EntityCentralIndexKey_label_en-US" xlink:label="lab_dei_EntityCentralIndexKey" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Entity Central Index Key</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_EntityCentralIndexKey" xlink:href="https://xbrl.sec.gov/dei/2022/dei-2022.xsd#dei_EntityCentralIndexKey"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_EntityCentralIndexKey" xlink:to="lab_dei_EntityCentralIndexKey" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AntidilutiveSecuritiesNameDomain_dcdf0f75-8121-4091-b8bc-0c2914439982_terseLabel_en-US" xlink:label="lab_us-gaap_AntidilutiveSecuritiesNameDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Antidilutive Securities, Name [Domain]</link:label>
    <link:label id="lab_us-gaap_AntidilutiveSecuritiesNameDomain_label_en-US" xlink:label="lab_us-gaap_AntidilutiveSecuritiesNameDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Antidilutive Securities, Name [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AntidilutiveSecuritiesNameDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_AntidilutiveSecuritiesNameDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AntidilutiveSecuritiesNameDomain" xlink:to="lab_us-gaap_AntidilutiveSecuritiesNameDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedWeightedAverageGrantDateFairValueRollForward_6b967833-00b8-4abf-ac50-fe4d86dd5a83_terseLabel_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedWeightedAverageGrantDateFairValueRollForward" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Weighted-Average Grant Date Fair Value per Share</link:label>
    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedWeightedAverageGrantDateFairValueRollForward_label_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedWeightedAverageGrantDateFairValueRollForward" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Share-Based Compensation Arrangement by Share-Based Payment Award, Equity Instruments Other than Options, Nonvested, Weighted Average Grant Date Fair Value [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedWeightedAverageGrantDateFairValueRollForward" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedWeightedAverageGrantDateFairValueRollForward"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedWeightedAverageGrantDateFairValueRollForward" xlink:to="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedWeightedAverageGrantDateFairValueRollForward" xlink:type="arc" order="1"/>
    <link:label id="lab_root_ShortTermWarrantMember_2fe1cc33-4247-4734-8ffb-68026d844d27_terseLabel_en-US" xlink:label="lab_root_ShortTermWarrantMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Short Term Warrant</link:label>
    <link:label id="lab_root_ShortTermWarrantMember_label_en-US" xlink:label="lab_root_ShortTermWarrantMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Short Term Warrant [Member]</link:label>
    <link:label id="lab_root_ShortTermWarrantMember_documentation_en-US" xlink:label="lab_root_ShortTermWarrantMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Short Term Warrant</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_root_ShortTermWarrantMember" xlink:href="root-20220930.xsd#root_ShortTermWarrantMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_root_ShortTermWarrantMember" xlink:to="lab_root_ShortTermWarrantMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ScheduleOfShareBasedCompensationArrangementsByShareBasedPaymentAwardTable_3be5a42e-1ecf-4121-9fcb-cf31c03c37dc_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfShareBasedCompensationArrangementsByShareBasedPaymentAwardTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Schedule of Share-based Compensation Arrangements by Share-based Payment Award [Table]</link:label>
    <link:label id="lab_us-gaap_ScheduleOfShareBasedCompensationArrangementsByShareBasedPaymentAwardTable_label_en-US" xlink:label="lab_us-gaap_ScheduleOfShareBasedCompensationArrangementsByShareBasedPaymentAwardTable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Schedule of Share-Based Compensation Arrangements by Share-Based Payment Award [Table]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfShareBasedCompensationArrangementsByShareBasedPaymentAwardTable" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ScheduleOfShareBasedCompensationArrangementsByShareBasedPaymentAwardTable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ScheduleOfShareBasedCompensationArrangementsByShareBasedPaymentAwardTable" xlink:to="lab_us-gaap_ScheduleOfShareBasedCompensationArrangementsByShareBasedPaymentAwardTable" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ReinsuranceRecoverablesAllowance_485dd0fb-d7fc-4b8e-b1bb-bfa3bb936b5a_terseLabel_en-US" xlink:label="lab_us-gaap_ReinsuranceRecoverablesAllowance" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Allowance for credit loss</link:label>
    <link:label id="lab_us-gaap_ReinsuranceRecoverablesAllowance_label_en-US" xlink:label="lab_us-gaap_ReinsuranceRecoverablesAllowance" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Reinsurance Recoverable, Allowance for Credit Loss</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ReinsuranceRecoverablesAllowance" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ReinsuranceRecoverablesAllowance"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ReinsuranceRecoverablesAllowance" xlink:to="lab_us-gaap_ReinsuranceRecoverablesAllowance" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_CityAreaCode_05a4ca22-ecb6-466c-bed6-00c77dcf1cdc_terseLabel_en-US" xlink:label="lab_dei_CityAreaCode" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">City Area Code</link:label>
    <link:label id="lab_dei_CityAreaCode_label_en-US" xlink:label="lab_dei_CityAreaCode" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">City Area Code</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_CityAreaCode" xlink:href="https://xbrl.sec.gov/dei/2022/dei-2022.xsd#dei_CityAreaCode"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_CityAreaCode" xlink:to="lab_dei_CityAreaCode" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_GeneralAndAdministrativeExpense_a8972fbe-2735-45e8-8448-44020db427a7_terseLabel_en-US" xlink:label="lab_us-gaap_GeneralAndAdministrativeExpense" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">General and administrative</link:label>
    <link:label id="lab_us-gaap_GeneralAndAdministrativeExpense_label_en-US" xlink:label="lab_us-gaap_GeneralAndAdministrativeExpense" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">General and Administrative Expense</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_GeneralAndAdministrativeExpense" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_GeneralAndAdministrativeExpense"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_GeneralAndAdministrativeExpense" xlink:to="lab_us-gaap_GeneralAndAdministrativeExpense" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AssetsAbstract_132b0a1d-d761-4208-9c35-a77b3119a600_terseLabel_en-US" xlink:label="lab_us-gaap_AssetsAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Assets</link:label>
    <link:label id="lab_us-gaap_AssetsAbstract_label_en-US" xlink:label="lab_us-gaap_AssetsAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Assets [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AssetsAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_AssetsAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AssetsAbstract" xlink:to="lab_us-gaap_AssetsAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LongtermDebtTypeDomain_37d5c016-0237-47a0-a572-ae58eb709a51_terseLabel_en-US" xlink:label="lab_us-gaap_LongtermDebtTypeDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Long-term Debt, Type [Domain]</link:label>
    <link:label id="lab_us-gaap_LongtermDebtTypeDomain_label_en-US" xlink:label="lab_us-gaap_LongtermDebtTypeDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Long-Term Debt, Type [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LongtermDebtTypeDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_LongtermDebtTypeDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LongtermDebtTypeDomain" xlink:to="lab_us-gaap_LongtermDebtTypeDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_OtherDebtSecuritiesMember_ade38899-70f5-4255-b4bf-0b2d2bb0d74b_terseLabel_en-US" xlink:label="lab_us-gaap_OtherDebtSecuritiesMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Other debt obligations</link:label>
    <link:label id="lab_us-gaap_OtherDebtSecuritiesMember_label_en-US" xlink:label="lab_us-gaap_OtherDebtSecuritiesMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Other Debt Obligations [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OtherDebtSecuritiesMember" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_OtherDebtSecuritiesMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_OtherDebtSecuritiesMember" xlink:to="lab_us-gaap_OtherDebtSecuritiesMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_StatementOfStockholdersEquityAbstract_label_en-US" xlink:label="lab_us-gaap_StatementOfStockholdersEquityAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Statement of Stockholders' Equity [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_StatementOfStockholdersEquityAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_StatementOfStockholdersEquityAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_StatementOfStockholdersEquityAbstract" xlink:to="lab_us-gaap_StatementOfStockholdersEquityAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_root_NonvestedSharesSubjectToRepurchaseMember_e5903f7e-8544-48e1-bef2-1fab14ccadf6_terseLabel_en-US" xlink:label="lab_root_NonvestedSharesSubjectToRepurchaseMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Redeemable convertible preferred stock (as converted to common stock)</link:label>
    <link:label id="lab_root_NonvestedSharesSubjectToRepurchaseMember_label_en-US" xlink:label="lab_root_NonvestedSharesSubjectToRepurchaseMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Nonvested Shares Subject To Repurchase [Member]</link:label>
    <link:label id="lab_root_NonvestedSharesSubjectToRepurchaseMember_documentation_en-US" xlink:label="lab_root_NonvestedSharesSubjectToRepurchaseMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Nonvested Shares Subject To Repurchase</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_root_NonvestedSharesSubjectToRepurchaseMember" xlink:href="root-20220930.xsd#root_NonvestedSharesSubjectToRepurchaseMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_root_NonvestedSharesSubjectToRepurchaseMember" xlink:to="lab_root_NonvestedSharesSubjectToRepurchaseMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DirectPremiumsWritten_83bbafd7-3e14-46a2-938e-637b65b14b71_terseLabel_en-US" xlink:label="lab_us-gaap_DirectPremiumsWritten" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Direct</link:label>
    <link:label id="lab_us-gaap_DirectPremiumsWritten_label_en-US" xlink:label="lab_us-gaap_DirectPremiumsWritten" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Direct Premiums Written</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DirectPremiumsWritten" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_DirectPremiumsWritten"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DirectPremiumsWritten" xlink:to="lab_us-gaap_DirectPremiumsWritten" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ProceedsFromMaturitiesPrepaymentsAndCallsOfAvailableForSaleSecurities_fcb97b46-90de-4817-b7ca-aa98f7d141d0_terseLabel_en-US" xlink:label="lab_us-gaap_ProceedsFromMaturitiesPrepaymentsAndCallsOfAvailableForSaleSecurities" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Proceeds from maturities, call and pay downs of investments</link:label>
    <link:label id="lab_us-gaap_ProceedsFromMaturitiesPrepaymentsAndCallsOfAvailableForSaleSecurities_label_en-US" xlink:label="lab_us-gaap_ProceedsFromMaturitiesPrepaymentsAndCallsOfAvailableForSaleSecurities" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Proceeds from Maturities, Prepayments and Calls of Debt Securities, Available-for-Sale</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ProceedsFromMaturitiesPrepaymentsAndCallsOfAvailableForSaleSecurities" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ProceedsFromMaturitiesPrepaymentsAndCallsOfAvailableForSaleSecurities"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ProceedsFromMaturitiesPrepaymentsAndCallsOfAvailableForSaleSecurities" xlink:to="lab_us-gaap_ProceedsFromMaturitiesPrepaymentsAndCallsOfAvailableForSaleSecurities" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesSingleMaturityDateAbstract_7cd78001-3509-4373-8c30-b52538ee9c89_terseLabel_en-US" xlink:label="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesSingleMaturityDateAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Fair Value</link:label>
    <link:label id="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesSingleMaturityDateAbstract_label_en-US" xlink:label="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesSingleMaturityDateAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt Securities, Available-for-Sale, Maturity, Allocated and Single Maturity Date, Fair Value [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesSingleMaturityDateAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_AvailableForSaleSecuritiesDebtMaturitiesSingleMaturityDateAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesSingleMaturityDateAbstract" xlink:to="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesSingleMaturityDateAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_NetCashProvidedByUsedInFinancingActivitiesAbstract_6ea280a7-5974-4786-b8cc-c1bcea3e87c4_terseLabel_en-US" xlink:label="lab_us-gaap_NetCashProvidedByUsedInFinancingActivitiesAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Cash flows from financing activities:</link:label>
    <link:label id="lab_us-gaap_NetCashProvidedByUsedInFinancingActivitiesAbstract_label_en-US" xlink:label="lab_us-gaap_NetCashProvidedByUsedInFinancingActivitiesAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Net Cash Provided by (Used in) Financing Activities [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NetCashProvidedByUsedInFinancingActivitiesAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_NetCashProvidedByUsedInFinancingActivitiesAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_NetCashProvidedByUsedInFinancingActivitiesAbstract" xlink:to="lab_us-gaap_NetCashProvidedByUsedInFinancingActivitiesAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ShareBasedCompensation_d263fbd0-bc19-43cf-a899-3b60b70917de_terseLabel_en-US" xlink:label="lab_us-gaap_ShareBasedCompensation" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Share-based compensation</link:label>
    <link:label id="lab_us-gaap_ShareBasedCompensation_label_en-US" xlink:label="lab_us-gaap_ShareBasedCompensation" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Share-Based Payment Arrangement, Noncash Expense</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShareBasedCompensation" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ShareBasedCompensation"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ShareBasedCompensation" xlink:to="lab_us-gaap_ShareBasedCompensation" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_PreferredStockLiquidationPreferenceValue_28e63c87-ae52-4df4-a4f5-69dc5d7c032f_terseLabel_en-US" xlink:label="lab_us-gaap_PreferredStockLiquidationPreferenceValue" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Preferred stock, liquidation preference</link:label>
    <link:label id="lab_us-gaap_PreferredStockLiquidationPreferenceValue_label_en-US" xlink:label="lab_us-gaap_PreferredStockLiquidationPreferenceValue" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Preferred Stock, Liquidation Preference, Value</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PreferredStockLiquidationPreferenceValue" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_PreferredStockLiquidationPreferenceValue"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PreferredStockLiquidationPreferenceValue" xlink:to="lab_us-gaap_PreferredStockLiquidationPreferenceValue" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_VariableRateAxis_767621c4-48a5-4d0a-a4d8-7d24d320eef0_terseLabel_en-US" xlink:label="lab_us-gaap_VariableRateAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Variable Rate [Axis]</link:label>
    <link:label id="lab_us-gaap_VariableRateAxis_label_en-US" xlink:label="lab_us-gaap_VariableRateAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Variable Rate [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_VariableRateAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_VariableRateAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_VariableRateAxis" xlink:to="lab_us-gaap_VariableRateAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ClassOfWarrantOrRightOutstanding_23d4999c-c1bf-453a-bd0f-dadbcf357629_terseLabel_en-US" xlink:label="lab_us-gaap_ClassOfWarrantOrRightOutstanding" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Warrants outstanding (in shares)</link:label>
    <link:label id="lab_us-gaap_ClassOfWarrantOrRightOutstanding_label_en-US" xlink:label="lab_us-gaap_ClassOfWarrantOrRightOutstanding" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Class of Warrant or Right, Outstanding</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ClassOfWarrantOrRightOutstanding" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ClassOfWarrantOrRightOutstanding"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ClassOfWarrantOrRightOutstanding" xlink:to="lab_us-gaap_ClassOfWarrantOrRightOutstanding" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_IncreaseDecreaseInOtherOperatingLiabilities_351068db-452e-4e32-b3ff-a7ff40dbf21a_terseLabel_en-US" xlink:label="lab_us-gaap_IncreaseDecreaseInOtherOperatingLiabilities" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Other liabilities</link:label>
    <link:label id="lab_us-gaap_IncreaseDecreaseInOtherOperatingLiabilities_label_en-US" xlink:label="lab_us-gaap_IncreaseDecreaseInOtherOperatingLiabilities" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Increase (Decrease) in Other Operating Liabilities</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncreaseDecreaseInOtherOperatingLiabilities" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_IncreaseDecreaseInOtherOperatingLiabilities"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IncreaseDecreaseInOtherOperatingLiabilities" xlink:to="lab_us-gaap_IncreaseDecreaseInOtherOperatingLiabilities" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_PaymentsToAcquirePropertyPlantAndEquipment_b0e997f4-0125-4d06-a766-5226d821a7a0_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_PaymentsToAcquirePropertyPlantAndEquipment" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Purchases of fixed assets</link:label>
    <link:label id="lab_us-gaap_PaymentsToAcquirePropertyPlantAndEquipment_label_en-US" xlink:label="lab_us-gaap_PaymentsToAcquirePropertyPlantAndEquipment" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Payments to Acquire Property, Plant, and Equipment</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PaymentsToAcquirePropertyPlantAndEquipment" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_PaymentsToAcquirePropertyPlantAndEquipment"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PaymentsToAcquirePropertyPlantAndEquipment" xlink:to="lab_us-gaap_PaymentsToAcquirePropertyPlantAndEquipment" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ScheduleOfEarningsPerShareBasicAndDilutedTableTextBlock_845f96df-ca07-4041-b0cd-6bc5a61384e0_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfEarningsPerShareBasicAndDilutedTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Schedule of Earnings Per Share</link:label>
    <link:label id="lab_us-gaap_ScheduleOfEarningsPerShareBasicAndDilutedTableTextBlock_label_en-US" xlink:label="lab_us-gaap_ScheduleOfEarningsPerShareBasicAndDilutedTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Schedule of Earnings Per Share, Basic and Diluted [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfEarningsPerShareBasicAndDilutedTableTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ScheduleOfEarningsPerShareBasicAndDilutedTableTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ScheduleOfEarningsPerShareBasicAndDilutedTableTextBlock" xlink:to="lab_us-gaap_ScheduleOfEarningsPerShareBasicAndDilutedTableTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_stpr_TX_4af382a5-84e8-4b9a-b294-4ee3e7c0ca3b_terseLabel_en-US" xlink:label="lab_stpr_TX" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Texas</link:label>
    <link:label id="lab_stpr_TX_label_en-US" xlink:label="lab_stpr_TX" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">TEXAS</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_stpr_TX" xlink:href="https://xbrl.sec.gov/stpr/2022/stpr-2022.xsd#stpr_TX"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_stpr_TX" xlink:to="lab_stpr_TX" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleRealizedLoss_79cbb764-d96c-4e32-9e79-b42197b6c74b_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleRealizedLoss" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Realized losses on investments</link:label>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleRealizedLoss_label_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleRealizedLoss" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt Securities, Available-for-Sale, Realized Loss</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtSecuritiesAvailableForSaleRealizedLoss" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_DebtSecuritiesAvailableForSaleRealizedLoss"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DebtSecuritiesAvailableForSaleRealizedLoss" xlink:to="lab_us-gaap_DebtSecuritiesAvailableForSaleRealizedLoss" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_UnearnedPremiums_9ab719c9-462a-4299-8d2a-606bb5d51576_terseLabel_en-US" xlink:label="lab_us-gaap_UnearnedPremiums" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Unearned premiums</link:label>
    <link:label id="lab_us-gaap_UnearnedPremiums_label_en-US" xlink:label="lab_us-gaap_UnearnedPremiums" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Unearned Premiums</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_UnearnedPremiums" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_UnearnedPremiums"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_UnearnedPremiums" xlink:to="lab_us-gaap_UnearnedPremiums" xlink:type="arc" order="1"/>
    <link:label id="lab_root_LiabilityForClaimsAndClaimsAdjustmentExpenseGross_4e0fc1aa-0cce-4391-b466-ff381a6feb65_terseLabel_en-US" xlink:label="lab_root_LiabilityForClaimsAndClaimsAdjustmentExpenseGross" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Loss and loss adjustment expense reserves</link:label>
    <link:label id="lab_root_LiabilityForClaimsAndClaimsAdjustmentExpenseGross_label_en-US" xlink:label="lab_root_LiabilityForClaimsAndClaimsAdjustmentExpenseGross" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Liability For Claims And Claims Adjustment Expense, Gross</link:label>
    <link:label id="lab_root_LiabilityForClaimsAndClaimsAdjustmentExpenseGross_documentation_en-US" xlink:label="lab_root_LiabilityForClaimsAndClaimsAdjustmentExpenseGross" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Liability For Claims And Claims Adjustment Expense, Gross</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_root_LiabilityForClaimsAndClaimsAdjustmentExpenseGross" xlink:href="root-20220930.xsd#root_LiabilityForClaimsAndClaimsAdjustmentExpenseGross"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_root_LiabilityForClaimsAndClaimsAdjustmentExpenseGross" xlink:to="lab_root_LiabilityForClaimsAndClaimsAdjustmentExpenseGross" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_RestructuringAndRelatedCostNumberOfPositionsEliminatedPeriodPercent_2d88619e-4eda-4a65-85e8-edb8ee04a814_terseLabel_en-US" xlink:label="lab_us-gaap_RestructuringAndRelatedCostNumberOfPositionsEliminatedPeriodPercent" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Workforce reduction, percent</link:label>
    <link:label id="lab_us-gaap_RestructuringAndRelatedCostNumberOfPositionsEliminatedPeriodPercent_label_en-US" xlink:label="lab_us-gaap_RestructuringAndRelatedCostNumberOfPositionsEliminatedPeriodPercent" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Restructuring and Related Cost, Number of Positions Eliminated, Period Percent</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_RestructuringAndRelatedCostNumberOfPositionsEliminatedPeriodPercent" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_RestructuringAndRelatedCostNumberOfPositionsEliminatedPeriodPercent"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_RestructuringAndRelatedCostNumberOfPositionsEliminatedPeriodPercent" xlink:to="lab_us-gaap_RestructuringAndRelatedCostNumberOfPositionsEliminatedPeriodPercent" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_RedeemableConvertiblePreferredStockMember_fd287e0d-31b2-468d-b772-9a8d9f49b021_terseLabel_en-US" xlink:label="lab_us-gaap_RedeemableConvertiblePreferredStockMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Nonvested shares subject to repurchase</link:label>
    <link:label id="lab_us-gaap_RedeemableConvertiblePreferredStockMember_label_en-US" xlink:label="lab_us-gaap_RedeemableConvertiblePreferredStockMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Redeemable Convertible Preferred Stock [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_RedeemableConvertiblePreferredStockMember" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_RedeemableConvertiblePreferredStockMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_RedeemableConvertiblePreferredStockMember" xlink:to="lab_us-gaap_RedeemableConvertiblePreferredStockMember" xlink:type="arc" order="1"/>
  </link:labelLink>
</link:linkbase>
