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    <link:label id="lab_us-gaap_StatementOfStockholdersEquityAbstract_87cdc4d5-c2ef-4ae7-af3a-78aeff4a049b_verboseLabel_en-US" xlink:label="lab_us-gaap_StatementOfStockholdersEquityAbstract" 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">Condensed consolidated statement of redeemable convertible preferred stock and stockholders equity:</link:label>
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    <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>
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    <link:label id="lab_us-gaap_LiabilityForClaimsAndClaimsAdjustmentExpense_f45c65be-358f-442f-a0e9-29209e4aed65_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>
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    <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>
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    <link:label id="lab_us-gaap_IncomeTaxDisclosureTextBlock_8f7689d1-5913-4de2-9e5b-b20c976b703f_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>
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    <link:label id="lab_us-gaap_IncreaseDecreaseInUnearnedPremiums_7d87eef1-eee4-49bf-ba45-2979242daca9_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>
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    <link:label id="lab_root_LongTermWarrantMember_15caacbc-eb50-4724-8c31-dc19ac8cede3_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-20230630.xsd#root_LongTermWarrantMember"/>
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    <link:label id="lab_us-gaap_PreferredStockParOrStatedValuePerShare_24d451db-b799-4944-ac5a-53d0b99785fa_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>
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    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedWeightedAverageGrantDateFairValueRollForward_9a33e5c4-a60e-4abe-b6c5-e7d21369be48_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>
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    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedWeightedAverageGrantDateFairValueRollForward" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedWeightedAverageGrantDateFairValueRollForward"/>
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    <link:label id="lab_us-gaap_EarningsPerShareDiluted_78890eb2-5bf6-4701-9136-bcf628132b7c_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>
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    <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_root_DebtInstrumentFloorInterestRate_c32cbb66-bd39-426c-ade2-da17163b543c_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>
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    <link:loc xlink:type="locator" xlink:label="loc_root_DebtInstrumentFloorInterestRate" xlink:href="root-20230630.xsd#root_DebtInstrumentFloorInterestRate"/>
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    <link:label id="lab_us-gaap_ReinsuranceRecoverablesAllowance_8c5c0078-83d4-498e-bec4-b19f15ad5fb3_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/2023/elts/us-gaap-2023.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_us-gaap_ReinsurancePayable_08398253-b918-4912-bae4-cdab29a1ad00_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/2023/elts/us-gaap-2023.xsd#us-gaap_ReinsurancePayable"/>
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    <link:label id="lab_stpr_TX_16366b3e-7c9f-4bde-9dcb-97eb97fd6a05_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>
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    <link:label id="lab_root_OtherInsuranceExpenseBenefitMember_e495224f-062d-4a66-beef-bcef5f642b7b_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>
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    <link:loc xlink:type="locator" xlink:label="loc_root_OtherInsuranceExpenseBenefitMember" xlink:href="root-20230630.xsd#root_OtherInsuranceExpenseBenefitMember"/>
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    <link:label id="lab_us-gaap_FairValueInputsLevel3Member_e6bb6765-66da-4069-836f-407e5190bcca_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>
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    <link:label id="lab_us-gaap_UnearnedPremiums_793ba7b0-a397-4103-8e4f-ed069ed92c1b_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>
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    <link:label id="lab_us-gaap_ResidentialMortgageBackedSecuritiesMember_8ce186c0-8e9f-4d32-a453-d5c352bad116_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>
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    <link:label id="lab_stpr_CO_8096955f-de4f-47cd-8000-ed808e394f81_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>
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    <link:label id="lab_us-gaap_ClassOfWarrantOrRightDomain_12d2bb1d-6710-49d1-8951-0f930541e55d_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>
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    <link:label id="lab_root_TermLoanCMember_f4d58ae8-fabf-4bf0-af4f-b6fa07402c1f_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>
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    <link:label id="lab_us-gaap_CommonStockSharesOutstanding_1bd010c1-e173-46de-88b2-cf060a550508_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>
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    <link:label id="lab_root_TechnologyAndDevelopmentExpenseMember_dbd96a0e-f464-4474-84ae-595a6ac819f6_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>
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    <link:label id="lab_us-gaap_ProceedsFromMaturitiesPrepaymentsAndCallsOfAvailableForSaleSecurities_84daed2d-ef89-48ea-8e12-7cd5fb916aaa_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>
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    <link:label id="lab_root_AllOtherStatesMember_206af61a-8a19-473d-943a-f8a17746abb2_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>
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    <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>
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    <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>
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    <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_CommonStockValue_269ec84a-9f87-48f2-82c9-4e23fd29ca37_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>
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    <link:label id="lab_us-gaap_GeneralAndAdministrativeExpense_fae454a1-359e-4c95-8624-855cb3177fec_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/2023/elts/us-gaap-2023.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_AvailableForSaleSecuritiesDebtMaturitiesAfterOneThroughFiveYearsFairValue_afad604a-391f-4a5c-9409-4e84eea69603_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>
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    <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>
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    <link:label id="lab_root_CreditRatingConcentrationRiskMember_d265ad60-f207-4e1c-91a1-badc6571727a_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>
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    <link:label id="lab_stpr_GA_500ba3ca-935c-4f5a-9d37-68e0dad2dd09_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>
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    <link:label id="lab_us-gaap_InterestPayableCurrentAndNoncurrent_19f4f28c-2f4d-4fe0-a186-f6308e805b98_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/2023/elts/us-gaap-2023.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_root_ClassOfWarrantOrRightNumberOfTranches_411b2508-581e-4ee1-bd9c-218bcc5cdcdc_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>
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    <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-20230630.xsd#root_ClassOfWarrantOrRightNumberOfTranches"/>
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    <link:label id="lab_us-gaap_RestrictedCash_7c8d6fe6-82a7-4f95-880d-dbf241279a76_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_cb240a1a-5de2-408d-ae33-4afc1be99bcd_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/2023/elts/us-gaap-2023.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_root_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsCeded_4da48f90-3595-45b8-a7a2-6a28e5dfd7c3_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>
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    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleRealizedGain_6ced8507-b4e7-4e2f-a949-d0f7c75f18a1_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>
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    <link:label id="lab_us-gaap_ScheduleOfShareBasedCompensationArrangementsByShareBasedPaymentAwardTable_ab8e1a59-e760-423f-b1f1-7a504cca6fb3_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>
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    <link:label id="lab_us-gaap_FeeIncome_5eb65fd3-07b8-4ed7-be53-c5d47fe0ed21_terseLabel_en-US" xlink:label="lab_us-gaap_FeeIncome" xlink: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 income</link:label>
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    <link:label id="lab_us-gaap_ConcentrationRiskByTypeAxis_6db00131-b63c-43b3-9b72-9b5bfd854bc1_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>
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    <link:label id="lab_us-gaap_PreferredStockLiquidationPreferenceValue_400443ef-f822-4b8c-a9bc-4928d1415d6a_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>
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    <link:label id="lab_us-gaap_EarningsPerShareTextBlock_7b813519-bad1-41f6-948c-e05be4ccca7f_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>
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    <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>
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    <link:label id="lab_root_CarvanaMember_462c4b5d-b917-4d75-ab53-004d004f3aef_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>
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    <link:label id="lab_us-gaap_ScheduleOfShareBasedCompensationStockOptionsActivityTableTextBlock_efbe46f8-a9cc-496a-9c1e-3c6b5eb84dd3_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>
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    <link:label id="lab_us-gaap_PremiumsReceivableAllowanceForDoubtfulAccounts_394c2004-6420-4df4-8cf7-990d8ab7f3ec_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/2023/elts/us-gaap-2023.xsd#us-gaap_PremiumsReceivableAllowanceForDoubtfulAccounts"/>
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    <link:label id="lab_us-gaap_RestructuringAndRelatedCostExpectedCost1_08fc7264-1569-4d23-9291-d34626c42148_terseLabel_en-US" xlink:label="lab_us-gaap_RestructuringAndRelatedCostExpectedCost1" xlink: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 and related cost, expected cost</link:label>
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    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_RestructuringAndRelatedCostExpectedCost1" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_RestructuringAndRelatedCostExpectedCost1"/>
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    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleUnrealizedLossPositionFairValueTableTextBlock_538ae396-3e01-4188-8b71-899299f7f5a2_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>
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    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtSecuritiesAvailableForSaleUnrealizedLossPositionFairValueTableTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_DebtSecuritiesAvailableForSaleUnrealizedLossPositionFairValueTableTextBlock"/>
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    <link:label id="lab_us-gaap_IncreaseDecreaseInReinsuranceRecoverable_a23c4d70-3b64-48db-9b8f-afaa84415860_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>
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    <link:label id="lab_us-gaap_InvestmentIncomeInvestmentExpense_4657d056-5779-4ae9-9804-aedca4c7c15e_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>
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    <link:label id="lab_dei_EntityAddressCityOrTown_6b574743-66e4-4edf-b67e-e62f86ccfe72_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>
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    <link:label id="lab_srt_RevisionOfPriorPeriodErrorCorrectionAdjustmentMember_255b0e0e-7828-4e8b-a215-353b5cd17acc_terseLabel_en-US" xlink:label="lab_srt_RevisionOfPriorPeriodErrorCorrectionAdjustmentMember" xlink: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</link:label>
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    <link:label id="lab_us-gaap_AssumedPremiumsWritten_bf2b96dd-124b-48f9-b092-78239e21443b_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>
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    <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_ConsolidationPolicyTextBlock_838cfe0a-b039-4667-bdb8-0ccb2cc970c3_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>
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    <link:label id="lab_us-gaap_ProceedsFromIssuanceOfDebt_78d89fd1-5802-4589-99e1-4ca23b98df00_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, net of issuance costs</link:label>
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    <link:label id="lab_us-gaap_RestructuringCharges_0dffe426-0e67-45d9-9a76-5b370e931e7c_verboseLabel_en-US" xlink:label="lab_us-gaap_RestructuringCharges" 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">Expense incurred</link:label>
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    <link:label id="lab_dei_DocumentTransitionReport_c17ff73d-7ae2-4db5-91ac-8dc6dd5057a9_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>
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    <link:label id="lab_root_TechnologyAndDevelopmentExpense_69a129f4-7d31-4167-85a3-9624086d1b85_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>
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    <link:label id="lab_us-gaap_CommonStockSharesAuthorized_c217cb5d-7b20-4309-98a7-3f46dd49bb1a_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>
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    <link:label id="lab_us-gaap_AvailableForSaleSecuritiesDebtSecurities_132f6117-1ed6-4bd0-a055-5534764e8e38_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>
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    <link:label id="lab_us-gaap_ShortTermInvestmentsMember_4bc18851-0266-4ba6-9345-35eb80d3bf81_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>
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    <link:label id="lab_stpr_OK_57f5d74a-bc03-400c-ac17-416cb5f54107_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>
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    <link:label id="lab_us-gaap_ReinsuranceRecoverableForUnpaidClaimsAndClaimsAdjustments_4adb2a92-c8f8-47d7-a695-80de417f0566_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>
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    <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>
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    <link:label id="lab_us-gaap_AdjustmentsToReconcileNetIncomeLossToCashProvidedByUsedInOperatingActivitiesAbstract_bbadfad2-2a79-4e59-a10d-62b0c934bb52_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>
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    <link:label id="lab_us-gaap_RestructuringReserveRollForward_54ccb80a-1e9b-4ce2-9e48-7b720193fddf_terseLabel_en-US" xlink:label="lab_us-gaap_RestructuringReserveRollForward" xlink: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 activity:</link:label>
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    <link:label id="lab_us-gaap_MunicipalBondsMember_1aace2ef-22e5-41b5-a2cb-6f9db786a132_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>
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    <link:label id="lab_root_StandardPoorsAPlusAAMinusRatingMember_cd38e48c-8ed4-4406-becd-e6e3ac7c7085_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>
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    <link:label id="lab_us-gaap_DirectPremiumsWritten_df4df55d-7583-4c18-97d5-24309f65d2b3_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>
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    <link:label id="lab_dei_EntityCentralIndexKey_25c0cba0-43b6-4e5b-a4dd-4d14db7cfc70_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>
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    <link:label id="lab_us-gaap_ClassOfWarrantOrRightAxis_4ae8b560-9221-4288-beea-f5a8c65a52ee_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>
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    <link:label id="lab_us-gaap_AllocatedShareBasedCompensationExpense_083fc328-2eb5-4703-913a-98c509135281_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>
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    <link:label id="lab_us-gaap_IncomeTaxExpenseBenefit_daf34530-2d32-4a47-92ae-596954f67dcb_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>
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    <link:label id="lab_us-gaap_FairValueDisclosuresTextBlock_c6f85934-39d4-40df-b3f3-f4fa492846b8_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>
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    <link:label id="lab_us-gaap_OtherRestructuringMember_ce9da66a-191d-45b0-8fd8-6fc481058afe_terseLabel_en-US" xlink:label="lab_us-gaap_OtherRestructuringMember" xlink: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 costs</link:label>
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    <link:label id="lab_us-gaap_OtherComprehensiveIncomeLossNetOfTaxPortionAttributableToParent_4674ad55-d2f5-4afa-be35-11f156bab18a_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_df57aa05-0869-4b21-9b9e-4079e8d71561_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>
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    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPosition12MonthsOrLongerAccumulatedLoss_385b57dd-27a0-4689-9d7e-ba2ef9c5df2f_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>
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    <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>
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    <link:label id="lab_us-gaap_LongtermDebtTypeAxis_228523e7-12b8-44e9-9199-3efa27547f64_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>
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    <link:label id="lab_us-gaap_TemporaryEquitySharesOutstanding_9f775184-7654-4921-a2dc-bd166cd2d4c9_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>
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    <link:label id="lab_us-gaap_CashAndCashEquivalentsAtCarryingValue_a3a41215-4fa9-4e8a-aa7d-c7ac776980e3_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>
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    <link:label id="lab_root_StandardPoorsBBBPlusBBBBBBMinusRatingMember_40170f3c-36cf-4647-8ec1-e9b309eef888_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>
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    <link:label id="lab_us-gaap_AssetsFairValueDisclosureAbstract_41002b4c-8359-4fe3-80cc-709d4f24285b_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>
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    <link:label id="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesWithinOneYearFairValue_da1a506b-a47e-4c5d-a3b6-5435b8339420_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>
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    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesWithinOneYearFairValue" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_AvailableForSaleSecuritiesDebtMaturitiesWithinOneYearFairValue"/>
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    <link:label id="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseNetAbstract_4dc3f20d-25fe-4d86-8341-65648a75e0cc_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/2023/elts/us-gaap-2023.xsd#us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseNetAbstract"/>
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    <link:label id="lab_us-gaap_DebtInstrumentBasisSpreadOnVariableRate1_2a014bd6-d305-4e17-b746-32b484c740c8_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>
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    <link:label id="lab_stpr_SC_652133ba-3918-4004-a967-9009d63dec46_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>
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    <link:label id="lab_us-gaap_SellingAndMarketingExpenseMember_0f27635d-bd35-4102-ae19-286e2df28bf6_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/2023/elts/us-gaap-2023.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_WeightedAverageNumberOfDilutedSharesOutstanding_512a5789-62b2-46e5-9b51-09eed0d6534a_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>
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    <link:label id="lab_root_DebtSecuritiesAvailableForSaleCurrentMember_299be6d6-a16e-497e-b3a2-873505de157e_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-20230630.xsd#root_DebtSecuritiesAvailableForSaleCurrentMember"/>
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    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleRealizedGainLoss_30efc8c4-ded1-4809-bd5d-c952173f9b9c_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 (losses) 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/2023/elts/us-gaap-2023.xsd#us-gaap_DebtSecuritiesAvailableForSaleRealizedGainLoss"/>
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    <link:label id="lab_us-gaap_OperatingExpensesAbstract_f9df386b-2f07-4191-9a70-f8254ba03be6_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/2023/elts/us-gaap-2023.xsd#us-gaap_OperatingExpensesAbstract"/>
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    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleRealizedLoss_73656f9a-3962-4f82-847c-d298b2cd4914_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/2023/elts/us-gaap-2023.xsd#us-gaap_DebtSecuritiesAvailableForSaleRealizedLoss"/>
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    <link:label id="lab_us-gaap_PaymentsToAcquirePropertyPlantAndEquipment_dd71ecd5-56b7-448e-8e12-065888bd9a2b_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>
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    <link:label id="lab_srt_RestatementAxis_f54a3661-8344-437b-8667-31792ba1d14e_terseLabel_en-US" xlink:label="lab_srt_RestatementAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Revision of Prior Period [Axis]</link:label>
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    <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>
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    <link:label id="lab_us-gaap_DirectPremiumsEarned_4bfc604f-24a4-41aa-bfff-d2979f1b2593_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>
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    <link:label id="lab_us-gaap_PremiumsReceivableAtCarryingValue_c52ddff5-9cda-4ca5-b365-298989bccbd3_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 $2.2 and $2.8 at June&#160;30, 2023 and December&#160;31, 2022, 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>
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    <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>
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    <link:label id="lab_us-gaap_EffectsOfReinsuranceTableTextBlock_5b61aec6-1d5b-42de-910d-ad899ec9fac8_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_778b4ec8-3330-4bea-be7f-fe6feeabb0ab_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 Premiums Written</link:label>
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    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsVestedInPeriodWeightedAverageGrantDateFairValue_a296ab5d-0529-42dc-8634-ea668a2629c1_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 (in dollars per share)</link:label>
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    <link:label id="lab_us-gaap_OperatingExpenses_5f85feb5-c672-40bb-a4fb-1f0f16d4c389_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>
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    <link:label id="lab_us-gaap_ReinsuranceRecoverablesOnPaidAndUnpaidLosses_5db3d8b0-5306-4dde-a8a2-7997ab2f5de5_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 $0.2 at June&#160;30, 2023 and December&#160;31, 2022</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>
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    <link:label id="lab_us-gaap_NetCashProvidedByUsedInFinancingActivitiesAbstract_0633e94e-52c0-4fb5-890c-22e086f4f728_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>
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    <link:label id="lab_us-gaap_ConcentrationRiskTypeDomain_994a755a-58ee-479f-b853-2dd74748653b_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>
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    <link:label id="lab_us-gaap_BondsMember_48099c83-726f-49ea-8e55-6797bac53027_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>
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    <link:label id="lab_us-gaap_OperatingIncomeLoss_4d43d9ed-31f7-4cff-a4ea-3c086a2676a3_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>
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    <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>
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    <link:label id="lab_us-gaap_RealizedInvestmentGainsLosses_c0d3dec2-d5d7-4405-b335-d2c2f679917c_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>
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    <link:label id="lab_us-gaap_ConcentrationRiskByBenchmarkAxis_f724631a-793b-44d9-b2e2-d6a573f53874_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>
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