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    <link:label id="lab_us-gaap_CurrentIncomeTaxExpenseBenefit_4b3973e3-c593-4d9f-a62b-f69f84f1c946_totalLabel_en-US" xlink:label="lab_us-gaap_CurrentIncomeTaxExpenseBenefit" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Total current</link:label>
    <link:label id="lab_us-gaap_CurrentIncomeTaxExpenseBenefit_label_en-US" xlink:label="lab_us-gaap_CurrentIncomeTaxExpenseBenefit" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Current Income Tax Expense (Benefit)</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CurrentIncomeTaxExpenseBenefit" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_CurrentIncomeTaxExpenseBenefit"/>
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    <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" xml:lang="en-US">Concentration Risk, Percentage</link:label>
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    <link:label id="lab_us-gaap_IncreaseDecreaseInOtherOperatingAssets_c98f8cd9-6fb1-4d19-bbc9-399eb11ab7f7_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_IncreaseDecreaseInOtherOperatingAssets" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Other assets</link:label>
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    <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" xml:lang="en-US">Consolidation, Policy [Policy Text Block]</link:label>
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    <link:label id="lab_us-gaap_ScheduleOfPropertyPlantAndEquipmentTable_2fd65e7d-b752-4be6-9c4e-9299de700a70_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfPropertyPlantAndEquipmentTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Property, Plant and Equipment [Table]</link:label>
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    <link:label id="lab_root_LongTermWarrantMember_226f65a1-84e7-493b-ba53-061c86e3479c_terseLabel_en-US" xlink:label="lab_root_LongTermWarrantMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Long Term Warrant</link:label>
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    <link:label id="lab_us-gaap_EffectiveIncomeTaxRateContinuingOperationsTaxRateReconciliationAbstract_e49a9412-0c3d-4d47-87b6-27a67be88482_terseLabel_en-US" xlink:label="lab_us-gaap_EffectiveIncomeTaxRateContinuingOperationsTaxRateReconciliationAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Percent</link:label>
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    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtSecuritiesAvailableForSaleTable" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.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_ecd_InsiderTradingPoliciesProcLineItems_label_en-US" xlink:label="lab_ecd_InsiderTradingPoliciesProcLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Insider Trading Policies and Procedures [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_InsiderTradingPoliciesProcLineItems" xlink:href="https://xbrl.sec.gov/ecd/2025/ecd-2025.xsd#ecd_InsiderTradingPoliciesProcLineItems"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_InsiderTradingPoliciesProcLineItems" xlink:to="lab_ecd_InsiderTradingPoliciesProcLineItems" xlink:type="arc" order="1"/>
    <link:label id="lab_root_DebtInstrumentFloorInterestRate_a677f335-e121-4316-b7cd-39c635d5e21d_terseLabel_en-US" xlink:label="lab_root_DebtInstrumentFloorInterestRate" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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" xml:lang="en-US">Debt Instrument, Floor Interest Rate</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_root_DebtInstrumentFloorInterestRate" xlink:href="root-20251231.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_CommonStockSharesAuthorized_cc2392ea-ac16-4044-beab-b48400147288_terseLabel_en-US" xlink:label="lab_us-gaap_CommonStockSharesAuthorized" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2025/elts/us-gaap-2025.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_us-gaap_PropertyPlantAndEquipmentTextBlock_7672a75d-a694-48ca-a443-59ac76ea5466_terseLabel_en-US" xlink:label="lab_us-gaap_PropertyPlantAndEquipmentTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Schedule of Fixed Assets</link:label>
    <link:label id="lab_us-gaap_PropertyPlantAndEquipmentTextBlock_label_en-US" xlink:label="lab_us-gaap_PropertyPlantAndEquipmentTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Property, Plant and Equipment [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PropertyPlantAndEquipmentTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_PropertyPlantAndEquipmentTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PropertyPlantAndEquipmentTextBlock" xlink:to="lab_us-gaap_PropertyPlantAndEquipmentTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_stpr_NV_99fc8b7b-544a-47ca-a978-3a422f0db5f4_terseLabel_en-US" xlink:label="lab_stpr_NV" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" xml:lang="en-US">NEVADA</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_stpr_NV" xlink:href="https://xbrl.sec.gov/stpr/2025/stpr-2025.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_LiabilitiesAndStockholdersEquityAbstract_d7ba1c80-dd66-4a08-922d-f65608b94560_terseLabel_en-US" xlink:label="lab_us-gaap_LiabilitiesAndStockholdersEquityAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Liabilities, Redeemable Convertible Preferred Stock and Stockholders&#8217; Equity</link:label>
    <link:label id="lab_us-gaap_LiabilitiesAndStockholdersEquityAbstract_2f52e1ef-1892-4ccc-9bd8-576a51ee7f84_verboseLabel_en-US" xlink:label="lab_us-gaap_LiabilitiesAndStockholdersEquityAbstract" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" 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" 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/2025/elts/us-gaap-2025.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_StateAndLocalJurisdictionMember_2c3f76ab-689a-4ac1-9902-2dfac8d06f31_terseLabel_en-US" xlink:label="lab_us-gaap_StateAndLocalJurisdictionMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">State and local (gross, apportioned)</link:label>
    <link:label id="lab_us-gaap_StateAndLocalJurisdictionMember_label_en-US" xlink:label="lab_us-gaap_StateAndLocalJurisdictionMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">State and Local Jurisdiction [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_StateAndLocalJurisdictionMember" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_StateAndLocalJurisdictionMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_StateAndLocalJurisdictionMember" xlink:to="lab_us-gaap_StateAndLocalJurisdictionMember" xlink:type="arc" order="1"/>
    <link:label id="lab_root_APICShareBasedPaymentArrangementIncreaseForCostRecognitionWarrants_68a2186c-965b-40de-a858-676336060f08_terseLabel_en-US" xlink:label="lab_root_APICShareBasedPaymentArrangementIncreaseForCostRecognitionWarrants" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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" 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-20251231.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_PremiumsReceivableAtCarryingValue_c384e7b1-20a6-4d2a-925f-c43dccef3461_terseLabel_en-US" xlink:label="lab_us-gaap_PremiumsReceivableAtCarryingValue" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Premiums receivable, net of allowance of $8.9 and $9.8 at December&#160;31, 2025 and December&#160;31, 2024, respectively</link:label>
    <link:label id="lab_us-gaap_PremiumsReceivableAtCarryingValue_e293aec3-a856-4a06-aceb-81a10062cfc1_verboseLabel_en-US" xlink:label="lab_us-gaap_PremiumsReceivableAtCarryingValue" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Premiums receivable</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" 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/2025/elts/us-gaap-2025.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_dei_CoverAbstract_33f55f20-7822-495a-8848-404ad0326ae7_terseLabel_en-US" xlink:label="lab_dei_CoverAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Cover [Abstract]</link:label>
    <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" 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/2025/dei-2025.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_CashAndCashEquivalentsFairValueDisclosure_366b8fd0-cdb3-4c69-9ce5-7c5ef57f891e_terseLabel_en-US" xlink:label="lab_us-gaap_CashAndCashEquivalentsFairValueDisclosure" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2025/elts/us-gaap-2025.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_PortionAtFairValueFairValueDisclosureMember_0ae6f92e-4656-43e7-9c06-21b14b24dd11_terseLabel_en-US" xlink:label="lab_us-gaap_PortionAtFairValueFairValueDisclosureMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2025/elts/us-gaap-2025.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_srt_MaximumMember_acd60882-02d9-46da-8a79-6e7b9ccd5a75_terseLabel_en-US" xlink:label="lab_srt_MaximumMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2025/elts/srt-2025.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_stpr_PA_517e1a09-d616-4dc5-9537-786f9680397e_terseLabel_en-US" xlink:label="lab_stpr_PA" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" xml:lang="en-US">PENNSYLVANIA</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_stpr_PA" xlink:href="https://xbrl.sec.gov/stpr/2025/stpr-2025.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_DebtSecuritiesAvailableForSaleUnrealizedLossPosition_88c81891-2e28-4f0d-9e82-e55d3e9b0f8a_totalLabel_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleUnrealizedLossPosition" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Total</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" 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/2025/elts/us-gaap-2025.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_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterTenYearsAmortizedCost_80821c4d-afaf-44d4-9fb4-8de5827ddc67_verboseLabel_en-US" xlink:label="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterTenYearsAmortizedCost" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" 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" 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/2025/elts/us-gaap-2025.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_InternalUseSoftwarePolicy_91aa886e-3e39-4074-af5f-36d74edba88a_terseLabel_en-US" xlink:label="lab_us-gaap_InternalUseSoftwarePolicy" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Internally Developed Software</link:label>
    <link:label id="lab_us-gaap_InternalUseSoftwarePolicy_label_en-US" xlink:label="lab_us-gaap_InternalUseSoftwarePolicy" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Internal Use Software, Policy [Policy Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_InternalUseSoftwarePolicy" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_InternalUseSoftwarePolicy"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_InternalUseSoftwarePolicy" xlink:to="lab_us-gaap_InternalUseSoftwarePolicy" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_NonPeoNeoAvgTotalCompAmt_terseLabel_en-US" xlink:label="lab_ecd_NonPeoNeoAvgTotalCompAmt" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Non-PEO NEO Average Total Compensation Amount</link:label>
    <link:label id="lab_ecd_NonPeoNeoAvgTotalCompAmt_label_en-US" xlink:label="lab_ecd_NonPeoNeoAvgTotalCompAmt" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Non-PEO NEO Average Total Compensation Amount</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_NonPeoNeoAvgTotalCompAmt" xlink:href="https://xbrl.sec.gov/ecd/2025/ecd-2025.xsd#ecd_NonPeoNeoAvgTotalCompAmt"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_NonPeoNeoAvgTotalCompAmt" xlink:to="lab_ecd_NonPeoNeoAvgTotalCompAmt" xlink:type="arc" order="1"/>
    <link:label id="lab_root_NetInvestmentIncomeMember_019b6e03-3216-7bd3-aa17-b46e337a7bb1_terseLabel_en-US" xlink:label="lab_root_NetInvestmentIncomeMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Net Investment Income</link:label>
    <link:label id="lab_root_NetInvestmentIncomeMember_label_en-US" xlink:label="lab_root_NetInvestmentIncomeMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Net Investment Income [Member]</link:label>
    <link:label id="lab_root_NetInvestmentIncomeMember_documentation_en-US" xlink:label="lab_root_NetInvestmentIncomeMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Net Investment Income</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_root_NetInvestmentIncomeMember" xlink:href="root-20251231.xsd#root_NetInvestmentIncomeMember"/>
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    <link:label id="lab_us-gaap_DebtInstrumentLineItems_af7aa9ad-9d93-4fe7-b996-38ff663abc89_terseLabel_en-US" xlink:label="lab_us-gaap_DebtInstrumentLineItems" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2025/elts/us-gaap-2025.xsd#us-gaap_DebtInstrumentLineItems"/>
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    <link:label id="lab_us-gaap_ScheduleOfShareBasedCompensationArrangementsByShareBasedPaymentAwardTable_170c4ba8-6891-4048-953e-2d0c67d48771_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfShareBasedCompensationArrangementsByShareBasedPaymentAwardTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2025/elts/us-gaap-2025.xsd#us-gaap_ScheduleOfShareBasedCompensationArrangementsByShareBasedPaymentAwardTable"/>
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    <link:label id="lab_root_ServiceBasedRestrictedStockUnitsMember_4217e578-9740-4049-a686-e00b5eef8c02_terseLabel_en-US" xlink:label="lab_root_ServiceBasedRestrictedStockUnitsMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Service-based restricted stock units</link:label>
    <link:label id="lab_root_ServiceBasedRestrictedStockUnitsMember_label_en-US" xlink:label="lab_root_ServiceBasedRestrictedStockUnitsMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Service-Based Restricted Stock Units [Member]</link:label>
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    <link:label id="lab_ecd_AdjToNonPeoNeoCompFnTextBlock_terseLabel_en-US" xlink:label="lab_ecd_AdjToNonPeoNeoCompFnTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Adjustment to Non-PEO NEO Compensation Footnote</link:label>
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    <link:loc xlink:type="locator" xlink:label="loc_ecd_AdjToNonPeoNeoCompFnTextBlock" xlink:href="https://xbrl.sec.gov/ecd/2025/ecd-2025.xsd#ecd_AdjToNonPeoNeoCompFnTextBlock"/>
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    <link:label id="lab_us-gaap_DirectPremiumsEarned_d29b07ab-8e5a-4dae-81c2-dd64e565b1a3_terseLabel_en-US" xlink:label="lab_us-gaap_DirectPremiumsEarned" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2025/elts/us-gaap-2025.xsd#us-gaap_DirectPremiumsEarned"/>
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    <link:label id="lab_srt_ExternalCreditRatingStandardPoorsMember_e5706cdc-1c53-4c2d-aabf-94064fbeb2cc_terseLabel_en-US" xlink:label="lab_srt_ExternalCreditRatingStandardPoorsMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2025/elts/srt-2025.xsd#srt_ExternalCreditRatingStandardPoorsMember"/>
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    <link:label id="lab_root_MahtiyarBonakdarpourMember_documentation_en-US" xlink:label="lab_root_MahtiyarBonakdarpourMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Mahtiyar Bonakdarpour</link:label>
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    <link:label id="lab_ecd_ForgoneRecoveryDueToDisqualificationOfTaxBenefitsAmt_terseLabel_en-US" xlink:label="lab_ecd_ForgoneRecoveryDueToDisqualificationOfTaxBenefitsAmt" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Forgone Recovery due to Disqualification of Tax Benefits, Amount</link:label>
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    <link:label id="lab_us-gaap_TemporaryEquityLineItems_c42cf9ed-6c2d-489b-b85d-202e2b09e096_terseLabel_en-US" xlink:label="lab_us-gaap_TemporaryEquityLineItems" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Temporary Equity [Line Items]</link:label>
    <link:label id="lab_us-gaap_TemporaryEquityLineItems_label_en-US" xlink:label="lab_us-gaap_TemporaryEquityLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Temporary Equity [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_TemporaryEquityLineItems" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_TemporaryEquityLineItems"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_TemporaryEquityLineItems" xlink:to="lab_us-gaap_TemporaryEquityLineItems" xlink:type="arc" order="1"/>
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    <link:label id="lab_root_ExercisePriceRangeOneMember_f705dc1d-2fc0-4590-8d9a-198764377728_terseLabel_en-US" xlink:label="lab_root_ExercisePriceRangeOneMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">$0.65 - $5.15</link:label>
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    <link:label id="lab_root_ExercisePriceRangeOneMember_documentation_en-US" xlink:label="lab_root_ExercisePriceRangeOneMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Exercise Price Range One</link:label>
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    <link:label id="lab_root_OperatingLossCarryforwardsNotSubjectToExpiration_1163cd11-8402-469c-bcda-4c3b55f2276f_terseLabel_en-US" xlink:label="lab_root_OperatingLossCarryforwardsNotSubjectToExpiration" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Carryforward Indefinitely</link:label>
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    <link:label id="lab_root_OperatingLossCarryforwardsNotSubjectToExpiration_documentation_en-US" xlink:label="lab_root_OperatingLossCarryforwardsNotSubjectToExpiration" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Operating Loss Carryforwards, Not Subject to Expiration</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_root_OperatingLossCarryforwardsNotSubjectToExpiration" xlink:href="root-20251231.xsd#root_OperatingLossCarryforwardsNotSubjectToExpiration"/>
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    <link:label id="lab_us-gaap_IncomeLossFromContinuingOperationsBeforeIncomeTaxesExtraordinaryItemsNoncontrollingInterest_883bbc7c-347c-4335-8ca4-5aa458345b64_totalLabel_en-US" xlink:label="lab_us-gaap_IncomeLossFromContinuingOperationsBeforeIncomeTaxesExtraordinaryItemsNoncontrollingInterest" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Income (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" 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/2025/elts/us-gaap-2025.xsd#us-gaap_IncomeLossFromContinuingOperationsBeforeIncomeTaxesExtraordinaryItemsNoncontrollingInterest"/>
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    <link:label id="lab_dei_EntityShellCompany_b063d672-9877-4f32-aa1d-c0c866381788_terseLabel_en-US" xlink:label="lab_dei_EntityShellCompany" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2025/dei-2025.xsd#dei_EntityShellCompany"/>
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    <link:label id="lab_us-gaap_PremiumsReceivableAllowanceForDoubtfulAccountsEstimationMethodologyPolicy_f6832596-bc11-44a2-8b6d-8ce1e5035e0f_terseLabel_en-US" xlink:label="lab_us-gaap_PremiumsReceivableAllowanceForDoubtfulAccountsEstimationMethodologyPolicy" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Premiums Receivable</link:label>
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    <link:label id="lab_us-gaap_DebtInstrumentTable_f80b23ad-37cf-41f4-b016-1bd00be17a45_terseLabel_en-US" xlink:label="lab_us-gaap_DebtInstrumentTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Schedule of Long-term Debt Instruments [Table]</link:label>
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    <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"/>
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    <link:label id="lab_us-gaap_StatementOfStockholdersEquityAbstract_19461490-e809-4a2a-860a-9ec82ab978fd_terseLabel_en-US" xlink:label="lab_us-gaap_StatementOfStockholdersEquityAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Statement of Stockholders' Equity [Abstract]</link:label>
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    <link:label id="lab_root_PurchaseObligationToBePaidAfterYearFour_2da647ae-d0d2-451f-92d8-a7378df4ef8a_terseLabel_en-US" xlink:label="lab_root_PurchaseObligationToBePaidAfterYearFour" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">2030 and thereafter</link:label>
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    <link:label id="lab_root_PurchaseObligationToBePaidAfterYearFour_documentation_en-US" xlink:label="lab_root_PurchaseObligationToBePaidAfterYearFour" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Purchase Obligation, to be Paid, after Year Four</link:label>
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    <link:label id="lab_ecd_AwardTmgMnpiCnsdrdFlag_label_en-US" xlink:label="lab_ecd_AwardTmgMnpiCnsdrdFlag" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Award Timing MNPI Considered [Flag]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_AwardTmgMnpiCnsdrdFlag" xlink:href="https://xbrl.sec.gov/ecd/2025/ecd-2025.xsd#ecd_AwardTmgMnpiCnsdrdFlag"/>
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    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleExcludingAccruedInterestNoncurrent_b98a57d3-037c-4284-ba6b-21889f515f95_terseLabel_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleExcludingAccruedInterestNoncurrent" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Fixed maturities available-for-sale, at fair value (amortized cost: $383.1 and $294.3 at December&#160;31, 2025 and December&#160;31, 2024, respectively)</link:label>
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    <link:label id="lab_us-gaap_ShareBasedCompensationSharesAuthorizedUnderStockOptionPlansByExercisePriceRangeAxis_049f60b0-742e-4863-8d0f-8c3bf9cf3743_terseLabel_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationSharesAuthorizedUnderStockOptionPlansByExercisePriceRangeAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Exercise Price Range [Axis]</link:label>
    <link:label id="lab_us-gaap_ShareBasedCompensationSharesAuthorizedUnderStockOptionPlansByExercisePriceRangeAxis_label_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationSharesAuthorizedUnderStockOptionPlansByExercisePriceRangeAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Exercise Price Range [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShareBasedCompensationSharesAuthorizedUnderStockOptionPlansByExercisePriceRangeAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_ShareBasedCompensationSharesAuthorizedUnderStockOptionPlansByExercisePriceRangeAxis"/>
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    <link:label id="lab_us-gaap_RestructuringReserve_dbfae29b-a512-4a30-b4cc-05a18dba57e5_periodEndLabel_en-US" xlink:label="lab_us-gaap_RestructuringReserve" xlink:role="http://www.xbrl.org/2003/role/periodEndLabel" xlink:type="resource" xml:lang="en-US">Restructuring liability, ending balance</link:label>
    <link:label id="lab_us-gaap_RestructuringReserve_label_en-US" xlink:label="lab_us-gaap_RestructuringReserve" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Restructuring Reserve</link:label>
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    <link:label id="lab_stpr_TX_b0d48f1e-c326-42e5-8815-feb89d50cc81_terseLabel_en-US" xlink:label="lab_stpr_TX" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" xml:lang="en-US">TEXAS</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_stpr_TX" xlink:href="https://xbrl.sec.gov/stpr/2025/stpr-2025.xsd#stpr_TX"/>
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    <link:label id="lab_us-gaap_IncomeLossFromContinuingOperationsBeforeIncomeTaxesDomestic_019c73d4-74dc-78ca-aac3-2c26667407e3_terseLabel_en-US" xlink:label="lab_us-gaap_IncomeLossFromContinuingOperationsBeforeIncomeTaxesDomestic" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Domestic</link:label>
    <link:label id="lab_us-gaap_IncomeLossFromContinuingOperationsBeforeIncomeTaxesDomestic_label_en-US" xlink:label="lab_us-gaap_IncomeLossFromContinuingOperationsBeforeIncomeTaxesDomestic" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Income (Loss) from Continuing Operations before Income Taxes, Domestic</link:label>
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    <link:label id="lab_us-gaap_ScheduleOfEmployeeServiceShareBasedCompensationAllocationOfRecognizedPeriodCostsTextBlock_18f792ef-718e-4d81-949f-fc383ac0f5fd_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfEmployeeServiceShareBasedCompensationAllocationOfRecognizedPeriodCostsTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2025/elts/us-gaap-2025.xsd#us-gaap_ScheduleOfEmployeeServiceShareBasedCompensationAllocationOfRecognizedPeriodCostsTextBlock"/>
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    <link:label id="lab_us-gaap_EffectiveIncomeTaxRateReconciliationNondeductibleExpenseAbstract_019c7a8b-f337-751c-9926-7bb0d412c0c7_terseLabel_en-US" xlink:label="lab_us-gaap_EffectiveIncomeTaxRateReconciliationNondeductibleExpenseAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Nontaxable and nondeductible items</link:label>
    <link:label id="lab_us-gaap_EffectiveIncomeTaxRateReconciliationNondeductibleExpenseAbstract_label_en-US" xlink:label="lab_us-gaap_EffectiveIncomeTaxRateReconciliationNondeductibleExpenseAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Effective Income Tax Rate Reconciliation, Nondeductible Expense, Percent [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EffectiveIncomeTaxRateReconciliationNondeductibleExpenseAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_EffectiveIncomeTaxRateReconciliationNondeductibleExpenseAbstract"/>
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    <link:label id="lab_root_AmendedTermLoanCExtinguishedAndModifiedMember_53c6f2e2-c944-4cc7-ba2a-01170243adb3_terseLabel_en-US" xlink:label="lab_root_AmendedTermLoanCExtinguishedAndModifiedMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Amended Term Loan C, Extinguished And Modified</link:label>
    <link:label id="lab_root_AmendedTermLoanCExtinguishedAndModifiedMember_label_en-US" xlink:label="lab_root_AmendedTermLoanCExtinguishedAndModifiedMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Amended Term Loan C, Extinguished And Modified [Member]</link:label>
    <link:label id="lab_root_AmendedTermLoanCExtinguishedAndModifiedMember_documentation_en-US" xlink:label="lab_root_AmendedTermLoanCExtinguishedAndModifiedMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Amended Term Loan C, Extinguished And Modified</link:label>
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    <link:label id="lab_dei_DocumentFiscalPeriodFocus_2ca1e805-59fe-4594-ad9d-8d21b83d548c_terseLabel_en-US" xlink:label="lab_dei_DocumentFiscalPeriodFocus" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" xml:lang="en-US">Document Fiscal Period Focus</link:label>
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    <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_ecd_AwardTmgMethodTextBlock_terseLabel_en-US" xlink:label="lab_ecd_AwardTmgMethodTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Award Timing Method</link:label>
    <link:label id="lab_ecd_AwardTmgMethodTextBlock_label_en-US" xlink:label="lab_ecd_AwardTmgMethodTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Award Timing Method [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_AwardTmgMethodTextBlock" xlink:href="https://xbrl.sec.gov/ecd/2025/ecd-2025.xsd#ecd_AwardTmgMethodTextBlock"/>
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    <link:label id="lab_us-gaap_FurnitureAndFixturesMember_30bfcba5-8566-4c41-985b-ac3ee8c0313d_terseLabel_en-US" xlink:label="lab_us-gaap_FurnitureAndFixturesMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Furniture</link:label>
    <link:label id="lab_us-gaap_FurnitureAndFixturesMember_label_en-US" xlink:label="lab_us-gaap_FurnitureAndFixturesMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Furniture and Fixtures [Member]</link:label>
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    <link:label id="lab_us-gaap_AwardTypeAxis_9c526e12-398e-4ff9-b361-8c3d58bbd3f8_terseLabel_en-US" xlink:label="lab_us-gaap_AwardTypeAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" xml:lang="en-US">Award Type [Axis]</link:label>
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    <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_srt_ParentCompanyMember_22daed3c-e841-4e98-87cb-1112fb5b7218_terseLabel_en-US" xlink:label="lab_srt_ParentCompanyMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Parent Company</link:label>
    <link:label id="lab_srt_ParentCompanyMember_label_en-US" xlink:label="lab_srt_ParentCompanyMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Parent Company [Member]</link:label>
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    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_ParentCompanyMember" xlink:to="lab_srt_ParentCompanyMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ResearchDevelopmentAndComputerSoftwarePolicyTextBlock_24dd722e-8e3a-4775-8f2c-fdb668ec8b18_terseLabel_en-US" xlink:label="lab_us-gaap_ResearchDevelopmentAndComputerSoftwarePolicyTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Technology and Development</link:label>
    <link:label id="lab_us-gaap_ResearchDevelopmentAndComputerSoftwarePolicyTextBlock_label_en-US" xlink:label="lab_us-gaap_ResearchDevelopmentAndComputerSoftwarePolicyTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Research, Development, and Computer Software, Policy [Policy Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ResearchDevelopmentAndComputerSoftwarePolicyTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_ResearchDevelopmentAndComputerSoftwarePolicyTextBlock"/>
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    <link:label id="lab_srt_EquityMethodInvesteeNameDomain_de30846a-2681-40c5-b7fa-06db76a71a34_terseLabel_en-US" xlink:label="lab_srt_EquityMethodInvesteeNameDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" xml:lang="en-US">Investment, Name [Domain]</link:label>
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    <link:label id="lab_us-gaap_ShareBasedCompensationOptionAndIncentivePlansPolicy_25ac2f86-aa6e-4958-96a0-fc91d9bf5270_terseLabel_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationOptionAndIncentivePlansPolicy" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Employee Share-Based Compensation</link:label>
    <link:label id="lab_us-gaap_ShareBasedCompensationOptionAndIncentivePlansPolicy_label_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationOptionAndIncentivePlansPolicy" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Share-Based Payment Arrangement [Policy Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShareBasedCompensationOptionAndIncentivePlansPolicy" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_ShareBasedCompensationOptionAndIncentivePlansPolicy"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ShareBasedCompensationOptionAndIncentivePlansPolicy" xlink:to="lab_us-gaap_ShareBasedCompensationOptionAndIncentivePlansPolicy" xlink:type="arc" order="1"/>
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    <link:label id="lab_us-gaap_LesseeOperatingLeaseLiabilityPaymentsDueYearFour_0c3b8dc2-fb9f-4c50-851d-16eaedc014da_terseLabel_en-US" xlink:label="lab_us-gaap_LesseeOperatingLeaseLiabilityPaymentsDueYearFour" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">2029</link:label>
    <link:label id="lab_us-gaap_LesseeOperatingLeaseLiabilityPaymentsDueYearFour_label_en-US" xlink:label="lab_us-gaap_LesseeOperatingLeaseLiabilityPaymentsDueYearFour" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Lessee, Operating Lease, Liability, to be Paid, Year Four</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LesseeOperatingLeaseLiabilityPaymentsDueYearFour" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_LesseeOperatingLeaseLiabilityPaymentsDueYearFour"/>
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    <link:label id="lab_root_DebtInstrumentCovenantQuarterlySubsidiarySurplusThreshold_cd2dfd55-94d8-4974-84d8-e254219fe149_terseLabel_en-US" xlink:label="lab_root_DebtInstrumentCovenantQuarterlySubsidiarySurplusThreshold" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Debt covenant, surplus threshold</link:label>
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    <link:label id="lab_root_DebtInstrumentCovenantQuarterlySubsidiarySurplusThreshold_documentation_en-US" xlink:label="lab_root_DebtInstrumentCovenantQuarterlySubsidiarySurplusThreshold" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Debt Instrument, Covenant, Quarterly Subsidiary Surplus Threshold</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_root_DebtInstrumentCovenantQuarterlySubsidiarySurplusThreshold" xlink:href="root-20251231.xsd#root_DebtInstrumentCovenantQuarterlySubsidiarySurplusThreshold"/>
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    <link:label id="lab_us-gaap_OperatingLossCarryforwardsTable_cc19ab8b-9e2c-4eb2-894b-ca9bcb203d25_terseLabel_en-US" xlink:label="lab_us-gaap_OperatingLossCarryforwardsTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Operating Loss Carryforwards [Table]</link:label>
    <link:label id="lab_us-gaap_OperatingLossCarryforwardsTable_label_en-US" xlink:label="lab_us-gaap_OperatingLossCarryforwardsTable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Operating Loss Carryforwards [Table]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OperatingLossCarryforwardsTable" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_OperatingLossCarryforwardsTable"/>
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    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EffectiveIncomeTaxRateReconciliationChangeInDeferredTaxAssetsValuationAllowance" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_EffectiveIncomeTaxRateReconciliationChangeInDeferredTaxAssetsValuationAllowance"/>
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    <link:label id="lab_us-gaap_GoodwillAndIntangibleAssetsIntangibleAssetsIndefiniteLivedPolicy_7e17484f-c253-4a33-b889-ff602d9fe8c2_terseLabel_en-US" xlink:label="lab_us-gaap_GoodwillAndIntangibleAssetsIntangibleAssetsIndefiniteLivedPolicy" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Indefinite-Lived Intangible Assets</link:label>
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    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_GoodwillAndIntangibleAssetsIntangibleAssetsIndefiniteLivedPolicy" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_GoodwillAndIntangibleAssetsIntangibleAssetsIndefiniteLivedPolicy"/>
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    <link:label id="lab_dei_EntityAddressCityOrTown_c2204a90-e37b-4fb4-a1ce-cd1be1ef3ff9_terseLabel_en-US" xlink:label="lab_dei_EntityAddressCityOrTown" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" xml:lang="en-US">Entity Address, City or Town</link:label>
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    <link:label id="lab_us-gaap_DeferredTaxAssetsNet_8f6fc865-a701-46a3-99ba-416ad2044032_totalLabel_en-US" xlink:label="lab_us-gaap_DeferredTaxAssetsNet" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Total deferred tax assets, less valuation allowance</link:label>
    <link:label id="lab_us-gaap_DeferredTaxAssetsNet_label_en-US" xlink:label="lab_us-gaap_DeferredTaxAssetsNet" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Deferred Tax Assets, Net of Valuation Allowance</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DeferredTaxAssetsNet" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_DeferredTaxAssetsNet"/>
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    <link:label id="lab_ecd_NonPeoNeoAvgCompActuallyPaidAmt_terseLabel_en-US" xlink:label="lab_ecd_NonPeoNeoAvgCompActuallyPaidAmt" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Non-PEO NEO Average Compensation Actually Paid Amount</link:label>
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    <link:label id="lab_us-gaap_IncomeStatementLocationDomain_60676120-936b-49f9-86e5-bb8031cda291_terseLabel_en-US" xlink:label="lab_us-gaap_IncomeStatementLocationDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Statement of Income Location, Balance [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" xml:lang="en-US">Statement of Income Location, Balance [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncomeStatementLocationDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_IncomeStatementLocationDomain"/>
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    <link:label id="lab_stpr_SC_6f4ebc1d-7d71-4b1f-a6a0-c2490bfd090d_terseLabel_en-US" xlink:label="lab_stpr_SC" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">South Carolina</link:label>
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    <link:label id="lab_us-gaap_StatutoryAccountingPracticesLineItems_2cc2f70f-da9a-4a73-8fd5-0fb2fba64d83_terseLabel_en-US" xlink:label="lab_us-gaap_StatutoryAccountingPracticesLineItems" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Statutory Accounting Practices [Line Items]</link:label>
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    <link:label id="lab_dei_EntityEmergingGrowthCompany_dad3c5a6-fe98-40a6-a01a-340faedb1e9d_terseLabel_en-US" xlink:label="lab_dei_EntityEmergingGrowthCompany" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Entity Emerging Growth Company</link:label>
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    <link:label id="lab_us-gaap_PaymentsToAcquireIntangibleAssets_c9eb16d3-3d73-449b-8b65-6622bbbc32cf_terseLabel_en-US" xlink:label="lab_us-gaap_PaymentsToAcquireIntangibleAssets" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Purchase of assets</link:label>
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    <link:label id="lab_us-gaap_DeferredFinanceCostsNet_9ee770bb-a9f8-451e-94e2-7e97062858ab_terseLabel_en-US" xlink:label="lab_us-gaap_DeferredFinanceCostsNet" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Debt issuance costs</link:label>
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    <link:label id="lab_us-gaap_RestrictedCashAndCashEquivalents_label_en-US" xlink:label="lab_us-gaap_RestrictedCashAndCashEquivalents" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Restricted Cash and Cash Equivalent</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_RestrictedCashAndCashEquivalents" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_RestrictedCashAndCashEquivalents"/>
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    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_RestructuringReserveRollForward" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_RestructuringReserveRollForward"/>
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    <link:label id="lab_us-gaap_CommonStockSharesOutstanding_1da3a41e-9b82-4393-8509-6792fc29ca53_terseLabel_en-US" xlink:label="lab_us-gaap_CommonStockSharesOutstanding" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Common stock, shares outstanding (in shares)</link:label>
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    <link:label id="lab_us-gaap_CommonStockSharesOutstanding_87f54fa0-d2f4-460e-a3cb-1e2a387f134e_periodEndLabel_en-US" xlink:label="lab_us-gaap_CommonStockSharesOutstanding" xlink:role="http://www.xbrl.org/2003/role/periodEndLabel" xlink:type="resource" 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" xml:lang="en-US">Common Stock, Shares, Outstanding</link:label>
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    <link:label id="lab_us-gaap_InsuranceAbstract_15648f02-a24a-498d-85ff-d20a18d48941_terseLabel_en-US" xlink:label="lab_us-gaap_InsuranceAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Insurance [Abstract]</link:label>
    <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" xml:lang="en-US">Insurance [Abstract]</link:label>
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    <link:label id="lab_us-gaap_SharebasedCompensationSharesAuthorizedUnderStockOptionPlansExercisePriceRangeExercisableOptionsWeightedAverageRemainingContractualTerm2_76031758-6cc5-4dca-93a8-4e0c299835e3_terseLabel_en-US" xlink:label="lab_us-gaap_SharebasedCompensationSharesAuthorizedUnderStockOptionPlansExercisePriceRangeExercisableOptionsWeightedAverageRemainingContractualTerm2" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Options exercisable, weighted-average remaining contractual term (in years)</link:label>
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    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SharebasedCompensationSharesAuthorizedUnderStockOptionPlansExercisePriceRangeExercisableOptionsWeightedAverageRemainingContractualTerm2" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_SharebasedCompensationSharesAuthorizedUnderStockOptionPlansExercisePriceRangeExercisableOptionsWeightedAverageRemainingContractualTerm2"/>
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    <link:label id="lab_us-gaap_CurrentIncomeTaxExpenseBenefitContinuingOperationsAbstract_81cbdd57-f7a5-42df-b357-9462e125b41b_terseLabel_en-US" xlink:label="lab_us-gaap_CurrentIncomeTaxExpenseBenefitContinuingOperationsAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Current:</link:label>
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    <link:label id="lab_us-gaap_ValuationAllowanceDeferredTaxAssetChangeInAmount_2fef1119-4b19-4004-8338-a0991fe1a0f9_terseLabel_en-US" xlink:label="lab_us-gaap_ValuationAllowanceDeferredTaxAssetChangeInAmount" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Valuation allowance decrease</link:label>
    <link:label id="lab_us-gaap_ValuationAllowanceDeferredTaxAssetChangeInAmount_label_en-US" xlink:label="lab_us-gaap_ValuationAllowanceDeferredTaxAssetChangeInAmount" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Valuation Allowance, Deferred Tax Asset, Increase (Decrease), Amount</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ValuationAllowanceDeferredTaxAssetChangeInAmount" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_ValuationAllowanceDeferredTaxAssetChangeInAmount"/>
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    <link:label id="lab_ecd_DvddsOrOthrErngsPdOnEqtyAwrdsNtOthrwsRflctdInTtlCompForCvrdYrMember_terseLabel_en-US" xlink:label="lab_ecd_DvddsOrOthrErngsPdOnEqtyAwrdsNtOthrwsRflctdInTtlCompForCvrdYrMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Dividends or Other Earnings Paid on Equity Awards not Otherwise Reflected in Total Compensation for Covered Year</link:label>
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    <link:label id="lab_us-gaap_AccountsPayableAndAccruedLiabilitiesCurrentAndNoncurrent_6af30693-12c5-4c36-8893-b9f533ca24b8_terseLabel_en-US" xlink:label="lab_us-gaap_AccountsPayableAndAccruedLiabilitiesCurrentAndNoncurrent" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Accounts payable and accrued expenses</link:label>
    <link:label id="lab_us-gaap_AccountsPayableAndAccruedLiabilitiesCurrentAndNoncurrent_3543c054-bb26-4930-9abd-dc1b9d9e74fc_verboseLabel_en-US" xlink:label="lab_us-gaap_AccountsPayableAndAccruedLiabilitiesCurrentAndNoncurrent" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" 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" xml:lang="en-US">Accounts Payable and Accrued Liabilities</link:label>
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    <link:label id="lab_us-gaap_ClaimsDevelopmentLineItems_104e069a-8021-4713-916b-555c84a1ab97_terseLabel_en-US" xlink:label="lab_us-gaap_ClaimsDevelopmentLineItems" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Claims Development [Line Items]</link:label>
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    <link:label id="lab_root_PaymentsForAssetAcquisitions_82b84276-336c-45bb-b1d4-82c1577eccf1_terseLabel_en-US" xlink:label="lab_root_PaymentsForAssetAcquisitions" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Purchases of indefinite-lived intangible assets and transaction costs</link:label>
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    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedRollForward_9e262a0b-a3c2-49c8-90b9-379e493b1bf9_verboseLabel_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedRollForward" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Number of Shares</link:label>
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    <link:label id="lab_dei_EntityAddressPostalZipCode_04663d1b-b16a-4c46-b11f-3cdf1657977d_terseLabel_en-US" xlink:label="lab_dei_EntityAddressPostalZipCode" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Entity Address, Postal Zip Code</link:label>
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    <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" xml:lang="en-US">Income Tax Expense (Benefit)</link:label>
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    <link:label id="lab_us-gaap_DebtInstrumentBasisSpreadOnVariableRate1_2cee430f-12d5-4b64-8563-97240132e724_terseLabel_en-US" xlink:label="lab_us-gaap_DebtInstrumentBasisSpreadOnVariableRate1" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Variable rate percentage (in percent)</link:label>
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    <link:label id="lab_us-gaap_OtherAssets_83b09409-d54a-4530-97a2-ad7ea1b773c1_terseLabel_en-US" xlink:label="lab_us-gaap_OtherAssets" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Other assets</link:label>
    <link:label id="lab_us-gaap_OtherAssets_19429ccb-cc93-4d2f-942b-55a258a0df16_verboseLabel_en-US" xlink:label="lab_us-gaap_OtherAssets" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Other assets</link:label>
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    <link:label id="lab_us-gaap_PreferredStockSharesIssued_71cc5319-9225-4157-a341-75b7b45c4984_terseLabel_en-US" xlink:label="lab_us-gaap_PreferredStockSharesIssued" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Preferred stock, issued (in shares)</link:label>
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    <link:label id="lab_us-gaap_FairValueByFairValueHierarchyLevelAxis_c3d85f6b-516b-4723-8276-b82ff14ebc60_terseLabel_en-US" xlink:label="lab_us-gaap_FairValueByFairValueHierarchyLevelAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Fair Value Hierarchy and NAV [Axis]</link:label>
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    <link:label id="lab_root_OperatingLossAndTaxCreditCarryforwardsNotSubjectToExpiration_09c78612-cbd2-49df-b905-c58755c39148_totalLabel_en-US" xlink:label="lab_root_OperatingLossAndTaxCreditCarryforwardsNotSubjectToExpiration" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Operating loss and tax credit carryforwards, not subject to expiration</link:label>
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    <link:label id="lab_us-gaap_PropertyPlantAndEquipmentGross_6afbfcf0-9f4e-4df9-97d0-5890216adce9_terseLabel_en-US" xlink:label="lab_us-gaap_PropertyPlantAndEquipmentGross" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Total fixed assets, at cost</link:label>
    <link:label id="lab_us-gaap_PropertyPlantAndEquipmentGross_label_en-US" xlink:label="lab_us-gaap_PropertyPlantAndEquipmentGross" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Property, Plant and Equipment, Gross</link:label>
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    <link:label id="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsAbstract_2ed93b5b-626a-4468-acbf-a0953beb9a0c_terseLabel_en-US" xlink:label="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Net incurred loss and LAE related to:</link:label>
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    <link:label id="lab_us-gaap_ReinsurancePayable_49ea8106-e98f-4b38-8e63-7978a408011b_terseLabel_en-US" xlink:label="lab_us-gaap_ReinsurancePayable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Reinsurance premiums payable</link:label>
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    <link:label id="lab_us-gaap_NetCashProvidedByUsedInOperatingActivities_b78f1c1c-fe9d-4771-9b6e-367267b605d9_totalLabel_en-US" xlink:label="lab_us-gaap_NetCashProvidedByUsedInOperatingActivities" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Net cash provided by (used in) operating activities</link:label>
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    <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" xml:lang="en-US">Cash Provided by (Used in) Operating Activity, Including Discontinued Operation</link:label>
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    <link:label id="lab_us-gaap_DebtInstrumentTerm_c7b2e836-c623-4ddc-8a75-4dec66cd47df_terseLabel_en-US" xlink:label="lab_us-gaap_DebtInstrumentTerm" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" xml:lang="en-US">Debt Instrument, Term</link:label>
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    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleExcludingAccruedInterest_8fd12c15-f933-4622-af65-8b9a2868279a_terseLabel_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleExcludingAccruedInterest" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Fair Value</link:label>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleExcludingAccruedInterest_ec4d8aab-3d6f-402a-8464-a54c212ad7e6_totalLabel_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleExcludingAccruedInterest" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Fair Value</link:label>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleExcludingAccruedInterest_daa38493-4124-4003-968e-16181878ac4b_verboseLabel_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleExcludingAccruedInterest" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Fixed maturities:</link:label>
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    <link:label id="lab_us-gaap_PropertyPlantAndEquipmentUsefulLife_25e8639f-ee2a-4d48-a0e6-94996f66a4d2_terseLabel_en-US" xlink:label="lab_us-gaap_PropertyPlantAndEquipmentUsefulLife" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Useful life</link:label>
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    <link:label id="lab_root_RegulatoryAssetRequirementSpecialDepositsAmortizedCost_3189a452-d4dc-4140-8e5c-85ad85e7b823_terseLabel_en-US" xlink:label="lab_root_RegulatoryAssetRequirementSpecialDepositsAmortizedCost" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Amortized costs of special deposits</link:label>
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    <link:label id="lab_us-gaap_IncomeTaxReconciliationNondeductibleExpenseShareBasedCompensationCost_5d6ec075-0506-4f7c-9391-7aa22bd8b530_terseLabel_en-US" xlink:label="lab_us-gaap_IncomeTaxReconciliationNondeductibleExpenseShareBasedCompensationCost" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Share-based compensation</link:label>
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    <link:label id="lab_us-gaap_DeferredTaxAssetsOperatingLossCarryforwards_06064f79-5775-4086-9e76-56e77ad9825b_terseLabel_en-US" xlink:label="lab_us-gaap_DeferredTaxAssetsOperatingLossCarryforwards" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Federal net operating loss carryforward</link:label>
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    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DeferredTaxAssetsOperatingLossCarryforwards" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_DeferredTaxAssetsOperatingLossCarryforwards"/>
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    <link:label id="lab_root_CapitalizedComputerSoftwareAmortizationPeriod_d2c3053f-6c79-4a9a-87e3-2514c0eeadcd_terseLabel_en-US" xlink:label="lab_root_CapitalizedComputerSoftwareAmortizationPeriod" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Amortization period</link:label>
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    <link:label id="lab_us-gaap_ReinsuranceRecoverablesOnPaidAndUnpaidLosses_eca4ba44-3118-4309-8676-54ff98272da0_terseLabel_en-US" xlink:label="lab_us-gaap_ReinsuranceRecoverablesOnPaidAndUnpaidLosses" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Reinsurance recoverable and receivable, net of allowance of $0.1 at December&#160;31, 2025 and December&#160;31, 2024</link:label>
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    <link:label id="lab_us-gaap_PropertyPlantAndEquipmentByTypeAxis_503f31a4-bca6-40d9-98d3-95e1a0187075_terseLabel_en-US" xlink:label="lab_us-gaap_PropertyPlantAndEquipmentByTypeAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Long-Lived Tangible Asset [Axis]</link:label>
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    <link:label id="lab_root_ProceedsFromDividendsFromSubsidiariesInvestingActivities_0a764b04-714d-4d8e-9dae-0f921d12c1b5_terseLabel_en-US" xlink:label="lab_root_ProceedsFromDividendsFromSubsidiariesInvestingActivities" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Dividends from subsidiaries</link:label>
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    <link:label id="lab_us-gaap_ValuationAllowancesAndReservesBalance_8de5746d-ffc6-459c-949b-60866f3b94b3_periodStartLabel_en-US" xlink:label="lab_us-gaap_ValuationAllowancesAndReservesBalance" xlink:role="http://www.xbrl.org/2003/role/periodStartLabel" xlink:type="resource" xml:lang="en-US">Balance at beginning of period</link:label>
    <link:label id="lab_us-gaap_ValuationAllowancesAndReservesBalance_99b7258f-2aa1-43f2-8841-30fd4d30a486_periodEndLabel_en-US" xlink:label="lab_us-gaap_ValuationAllowancesAndReservesBalance" xlink:role="http://www.xbrl.org/2003/role/periodEndLabel" xlink:type="resource" xml:lang="en-US">Balance at end of period</link:label>
    <link:label id="lab_us-gaap_ValuationAllowancesAndReservesBalance_label_en-US" xlink:label="lab_us-gaap_ValuationAllowancesAndReservesBalance" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">SEC Schedule, 12-09, Valuation Allowances and Reserves, Amount</link:label>
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    <link:label id="lab_root_AmendedTermLoanCBlackRockFundsMember_fe8c2657-bfa4-426b-a90c-97290eafbbaf_terseLabel_en-US" xlink:label="lab_root_AmendedTermLoanCBlackRockFundsMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Amended Term Loan C, Black Rock Funds</link:label>
    <link:label id="lab_root_AmendedTermLoanCBlackRockFundsMember_label_en-US" xlink:label="lab_root_AmendedTermLoanCBlackRockFundsMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Amended Term Loan C, Black Rock Funds [Member]</link:label>
    <link:label id="lab_root_AmendedTermLoanCBlackRockFundsMember_documentation_en-US" xlink:label="lab_root_AmendedTermLoanCBlackRockFundsMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Amended Term Loan C, Black Rock Funds</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_root_AmendedTermLoanCBlackRockFundsMember" xlink:href="root-20251231.xsd#root_AmendedTermLoanCBlackRockFundsMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_root_AmendedTermLoanCBlackRockFundsMember" xlink:to="lab_root_AmendedTermLoanCBlackRockFundsMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ShortdurationInsuranceContractsLiabilityForUnpaidClaimsAndAllocatedClaimAdjustmentExpenseNetNotSeparatelyPresented_019c400c-c39a-76f7-8fcb-2d84084684ea_terseLabel_en-US" xlink:label="lab_us-gaap_ShortdurationInsuranceContractsLiabilityForUnpaidClaimsAndAllocatedClaimAdjustmentExpenseNetNotSeparatelyPresented" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">All outstanding liabilities before 2021&#8212;net of reinsurance</link:label>
    <link:label id="lab_us-gaap_ShortdurationInsuranceContractsLiabilityForUnpaidClaimsAndAllocatedClaimAdjustmentExpenseNetNotSeparatelyPresented_label_en-US" xlink:label="lab_us-gaap_ShortdurationInsuranceContractsLiabilityForUnpaidClaimsAndAllocatedClaimAdjustmentExpenseNetNotSeparatelyPresented" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Short-Duration Insurance Contracts, Liability for Unpaid Claims and Allocated Claim Adjustment Expense, Net, Not Separately Presented</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShortdurationInsuranceContractsLiabilityForUnpaidClaimsAndAllocatedClaimAdjustmentExpenseNetNotSeparatelyPresented" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_ShortdurationInsuranceContractsLiabilityForUnpaidClaimsAndAllocatedClaimAdjustmentExpenseNetNotSeparatelyPresented"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ShortdurationInsuranceContractsLiabilityForUnpaidClaimsAndAllocatedClaimAdjustmentExpenseNetNotSeparatelyPresented" xlink:to="lab_us-gaap_ShortdurationInsuranceContractsLiabilityForUnpaidClaimsAndAllocatedClaimAdjustmentExpenseNetNotSeparatelyPresented" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ScheduleOfUnrecognizedCompensationCostNonvestedAwardsTableTextBlock_94664ec0-1bf5-4a04-a9e7-85bc194dc245_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfUnrecognizedCompensationCostNonvestedAwardsTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Schedule of Restricted Stock and Unvested Stock Options</link:label>
    <link:label id="lab_us-gaap_ScheduleOfUnrecognizedCompensationCostNonvestedAwardsTableTextBlock_label_en-US" xlink:label="lab_us-gaap_ScheduleOfUnrecognizedCompensationCostNonvestedAwardsTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Share-Based Payment Arrangement, Nonvested Award, Cost [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfUnrecognizedCompensationCostNonvestedAwardsTableTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_ScheduleOfUnrecognizedCompensationCostNonvestedAwardsTableTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ScheduleOfUnrecognizedCompensationCostNonvestedAwardsTableTextBlock" xlink:to="lab_us-gaap_ScheduleOfUnrecognizedCompensationCostNonvestedAwardsTableTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_EntityCentralIndexKey_3ad6f3c9-999d-4855-ba42-1a5b28372e89_terseLabel_en-US" xlink:label="lab_dei_EntityCentralIndexKey" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2025/dei-2025.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_ecd_PeoName_terseLabel_en-US" xlink:label="lab_ecd_PeoName" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">PEO Name</link:label>
    <link:label id="lab_ecd_PeoName_label_en-US" xlink:label="lab_ecd_PeoName" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">PEO Name</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_PeoName" xlink:href="https://xbrl.sec.gov/ecd/2025/ecd-2025.xsd#ecd_PeoName"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_PeoName" xlink:to="lab_ecd_PeoName" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_Revenues_e67e9ab8-9f7f-4222-8e44-b2fe34d33a7d_totalLabel_en-US" xlink:label="lab_us-gaap_Revenues" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" 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" 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/2025/elts/us-gaap-2025.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_ecd_FrValAsOfPrrYrEndOfEqtyAwrdsGrntdInPrrYrsFldVstngCondsDrngCvrdYrMember_terseLabel_en-US" xlink:label="lab_ecd_FrValAsOfPrrYrEndOfEqtyAwrdsGrntdInPrrYrsFldVstngCondsDrngCvrdYrMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Prior Year End Fair Value of Equity Awards Granted in Any Prior Year that Fail to Meet Applicable Vesting Conditions During Covered Year</link:label>
    <link:label id="lab_ecd_FrValAsOfPrrYrEndOfEqtyAwrdsGrntdInPrrYrsFldVstngCondsDrngCvrdYrMember_label_en-US" xlink:label="lab_ecd_FrValAsOfPrrYrEndOfEqtyAwrdsGrntdInPrrYrsFldVstngCondsDrngCvrdYrMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Prior Year End Fair Value of Equity Awards Granted in Any Prior Year that Fail to Meet Applicable Vesting Conditions During Covered Year [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_FrValAsOfPrrYrEndOfEqtyAwrdsGrntdInPrrYrsFldVstngCondsDrngCvrdYrMember" xlink:href="https://xbrl.sec.gov/ecd/2025/ecd-2025.xsd#ecd_FrValAsOfPrrYrEndOfEqtyAwrdsGrntdInPrrYrsFldVstngCondsDrngCvrdYrMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_FrValAsOfPrrYrEndOfEqtyAwrdsGrntdInPrrYrsFldVstngCondsDrngCvrdYrMember" xlink:to="lab_ecd_FrValAsOfPrrYrEndOfEqtyAwrdsGrntdInPrrYrsFldVstngCondsDrngCvrdYrMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_PurchaseObligationDueInSecondYear_25611ede-ce8c-47c7-ab90-7ed8057e43f6_terseLabel_en-US" xlink:label="lab_us-gaap_PurchaseObligationDueInSecondYear" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">2027</link:label>
    <link:label id="lab_us-gaap_PurchaseObligationDueInSecondYear_label_en-US" xlink:label="lab_us-gaap_PurchaseObligationDueInSecondYear" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Purchase Obligation, to be Paid, Year Two</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PurchaseObligationDueInSecondYear" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_PurchaseObligationDueInSecondYear"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PurchaseObligationDueInSecondYear" xlink:to="lab_us-gaap_PurchaseObligationDueInSecondYear" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FairValueBalanceSheetGroupingFinancialStatementCaptionsLineItems_4db51032-85cf-4cb8-9611-15bded2892c1_terseLabel_en-US" xlink:label="lab_us-gaap_FairValueBalanceSheetGroupingFinancialStatementCaptionsLineItems" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2025/elts/us-gaap-2025.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_PaymentsToAcquireInterestInSubsidiariesAndAffiliates_e28180ef-3bb0-450e-beaf-f9a8600d93a9_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_PaymentsToAcquireInterestInSubsidiariesAndAffiliates" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Investment in subsidiaries</link:label>
    <link:label id="lab_us-gaap_PaymentsToAcquireInterestInSubsidiariesAndAffiliates_label_en-US" xlink:label="lab_us-gaap_PaymentsToAcquireInterestInSubsidiariesAndAffiliates" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Payments to Acquire Interest in Subsidiaries and Affiliates</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PaymentsToAcquireInterestInSubsidiariesAndAffiliates" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_PaymentsToAcquireInterestInSubsidiariesAndAffiliates"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PaymentsToAcquireInterestInSubsidiariesAndAffiliates" xlink:to="lab_us-gaap_PaymentsToAcquireInterestInSubsidiariesAndAffiliates" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_OutstandingAggtErrCompAmt_terseLabel_en-US" xlink:label="lab_ecd_OutstandingAggtErrCompAmt" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Outstanding Aggregate Erroneous Compensation Amount</link:label>
    <link:label id="lab_ecd_OutstandingAggtErrCompAmt_label_en-US" xlink:label="lab_ecd_OutstandingAggtErrCompAmt" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Outstanding Aggregate Erroneous Compensation Amount</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_OutstandingAggtErrCompAmt" xlink:href="https://xbrl.sec.gov/ecd/2025/ecd-2025.xsd#ecd_OutstandingAggtErrCompAmt"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_OutstandingAggtErrCompAmt" xlink:to="lab_ecd_OutstandingAggtErrCompAmt" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaims1_da3f6a7d-c2fc-4c9c-bec1-d9d17747171a_verboseLabel_en-US" xlink:label="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaims1" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Loss and loss adjustment expenses</link:label>
    <link:label id="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaims1_0fd398d4-b9c1-49cb-8c49-38f08805bb41_totalLabel_en-US" xlink:label="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaims1" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Net losses and LAE 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" 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/2025/elts/us-gaap-2025.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_root_TechnologyAndDevelopmentExpenseMember_017e8dee-2965-4543-9500-722c3d900638_terseLabel_en-US" xlink:label="lab_root_TechnologyAndDevelopmentExpenseMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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" xml:lang="en-US">Technology And Development Expense</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_root_TechnologyAndDevelopmentExpenseMember" xlink:href="root-20251231.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_root_ExercisePriceRangeThreeMember_6dff98a3-6511-470e-a970-8059344fab56_terseLabel_en-US" xlink:label="lab_root_ExercisePriceRangeThreeMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">$43.20 - $231.66</link:label>
    <link:label id="lab_root_ExercisePriceRangeThreeMember_label_en-US" xlink:label="lab_root_ExercisePriceRangeThreeMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Exercise Price Range Three [Member]</link:label>
    <link:label id="lab_root_ExercisePriceRangeThreeMember_documentation_en-US" xlink:label="lab_root_ExercisePriceRangeThreeMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Exercise Price Range Three</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_root_ExercisePriceRangeThreeMember" xlink:href="root-20251231.xsd#root_ExercisePriceRangeThreeMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_root_ExercisePriceRangeThreeMember" xlink:to="lab_root_ExercisePriceRangeThreeMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ShareBasedCompensationAwardTrancheOneMember_e7024244-99e1-4041-a2c6-1974cf12b536_terseLabel_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationAwardTrancheOneMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2025/elts/us-gaap-2025.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_StatutoryAccountingPracticesStatutoryNetIncomeAmount_62d0e07a-5c5e-45f2-8942-8efba17a18f4_verboseLabel_en-US" xlink:label="lab_us-gaap_StatutoryAccountingPracticesStatutoryNetIncomeAmount" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Statutory Net Income (Loss)</link:label>
    <link:label id="lab_us-gaap_StatutoryAccountingPracticesStatutoryNetIncomeAmount_label_en-US" xlink:label="lab_us-gaap_StatutoryAccountingPracticesStatutoryNetIncomeAmount" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Statutory Accounting Practices, Statutory Net Income Amount</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_StatutoryAccountingPracticesStatutoryNetIncomeAmount" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_StatutoryAccountingPracticesStatutoryNetIncomeAmount"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_StatutoryAccountingPracticesStatutoryNetIncomeAmount" xlink:to="lab_us-gaap_StatutoryAccountingPracticesStatutoryNetIncomeAmount" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_IncomeTaxReconciliationNondeductibleExpenseAbstract_019c7a62-ab45-76a8-9bb2-95453b49be10_terseLabel_en-US" xlink:label="lab_us-gaap_IncomeTaxReconciliationNondeductibleExpenseAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Nontaxable and nondeductible items</link:label>
    <link:label id="lab_us-gaap_IncomeTaxReconciliationNondeductibleExpenseAbstract_label_en-US" xlink:label="lab_us-gaap_IncomeTaxReconciliationNondeductibleExpenseAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Effective Income Tax Rate Reconciliation, Nondeductible Expense, Amount [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncomeTaxReconciliationNondeductibleExpenseAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_IncomeTaxReconciliationNondeductibleExpenseAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IncomeTaxReconciliationNondeductibleExpenseAbstract" xlink:to="lab_us-gaap_IncomeTaxReconciliationNondeductibleExpenseAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_PremiumsWrittenNet_a1af5f41-a85b-4595-9fe0-0c23bf02887d_totalLabel_en-US" xlink:label="lab_us-gaap_PremiumsWrittenNet" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" 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" 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/2025/elts/us-gaap-2025.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_PremiumsReceivableAllowanceForDoubtfulAccounts_9bf2cb93-19d6-454d-9519-43ac0632a4b1_terseLabel_en-US" xlink:label="lab_us-gaap_PremiumsReceivableAllowanceForDoubtfulAccounts" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2025/elts/us-gaap-2025.xsd#us-gaap_PremiumsReceivableAllowanceForDoubtfulAccounts"/>
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    <link:label id="lab_us-gaap_ClassOfWarrantOrRightExercisePriceOfWarrantsOrRights1_f41763c6-d905-4442-9960-bae33b292801_terseLabel_en-US" xlink:label="lab_us-gaap_ClassOfWarrantOrRightExercisePriceOfWarrantsOrRights1" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Exercise price of warrants (in dollars per share)</link:label>
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    <link:label id="lab_us-gaap_TemporaryEquityCarryingAmountAttributableToParent_1e5ebf96-95aa-42d1-b3a0-6fe450e410fd_verboseLabel_en-US" xlink:label="lab_us-gaap_TemporaryEquityCarryingAmountAttributableToParent" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Redeemable convertible preferred stock, $0.0001 par value, 14.1 shares issued and outstanding at December&#160;31, 2025 and December&#160;31, 2024 (redemption value of $126.5) (Note 11)</link:label>
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    <link:label id="lab_us-gaap_TemporaryEquityCarryingAmountAttributableToParent_a883bc0a-0439-48d9-b442-962dd432c422_terseLabel_en-US" xlink:label="lab_us-gaap_TemporaryEquityCarryingAmountAttributableToParent" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Redeemable convertible preferred stock, $0.0001 par value, 14.1 shares issued and outstanding at December&#160;31, 2025 and December&#160;31, 2024 (redemption value of $126.5)</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" xml:lang="en-US">Temporary Equity, Carrying Amount, Attributable to Parent</link:label>
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    <link:label id="lab_ecd_AwardExrcPrice_label_en-US" xlink:label="lab_ecd_AwardExrcPrice" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Award Exercise Price</link:label>
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    <link:label id="lab_us-gaap_ClassOfStockDomain_208bff36-2db9-4eb6-b779-a141a9d3382a_terseLabel_en-US" xlink:label="lab_us-gaap_ClassOfStockDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" xml:lang="en-US">Class of Stock [Domain]</link:label>
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    <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_EffectiveIncomeTaxRateReconciliationAtFederalStatutoryIncomeTaxRate_e680ee6c-9e0b-4c7d-8422-a311690c98b1_terseLabel_en-US" xlink:label="lab_us-gaap_EffectiveIncomeTaxRateReconciliationAtFederalStatutoryIncomeTaxRate" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Statutory United States federal income tax expense</link:label>
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    <link:label id="lab_us-gaap_ClassOfWarrantOrRightDomain_978ef01e-1524-4581-a5b6-e0d7b0b2884c_terseLabel_en-US" xlink:label="lab_us-gaap_ClassOfWarrantOrRightDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" xml:lang="en-US">Class of Warrant or Right [Domain]</link:label>
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    <link:label id="lab_us-gaap_VestingDomain_820e6b0b-55cd-451a-b5f8-4b56d0d2b7bf_terseLabel_en-US" xlink:label="lab_us-gaap_VestingDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2025/elts/us-gaap-2025.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_root_EffectiveIncomeTaxOperatingLossCarryforwardsStateAndLocalAmount_12cde740-08a8-479f-a367-4f282f62ba7b_terseLabel_en-US" xlink:label="lab_root_EffectiveIncomeTaxOperatingLossCarryforwardsStateAndLocalAmount" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">State net operating loss</link:label>
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    <link:label id="lab_ecd_VstngDtFrValOfEqtyAwrdsGrntdAndVstdInCvrdYrMember_terseLabel_en-US" xlink:label="lab_ecd_VstngDtFrValOfEqtyAwrdsGrntdAndVstdInCvrdYrMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Vesting Date Fair Value of Equity Awards Granted and Vested in Covered Year</link:label>
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    <link:label id="lab_us-gaap_PremiumsWrittenGross_79d13b73-36dd-4d92-9497-3c245f638a0f_terseLabel_en-US" xlink:label="lab_us-gaap_PremiumsWrittenGross" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Total</link:label>
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    <link:label id="lab_dei_EntityAddressAddressLine1_a6ecfaf6-e898-4fa8-9d22-ca8bd66afed1_terseLabel_en-US" xlink:label="lab_dei_EntityAddressAddressLine1" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Entity Address, Address Line One</link:label>
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    <link:label id="lab_us-gaap_ScheduleOfShareBasedCompensationSharesAuthorizedUnderStockOptionPlansByExercisePriceRangeTextBlock_df08a12f-3757-4191-8e5a-9e81b44c3a0c_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfShareBasedCompensationSharesAuthorizedUnderStockOptionPlansByExercisePriceRangeTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Schedule of Exercise Price Range</link:label>
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    <link:label id="lab_us-gaap_AccumulatedOtherComprehensiveIncomeMember_acb5a3cd-7128-4107-bcd1-a6a41a799525_terseLabel_en-US" xlink:label="lab_us-gaap_AccumulatedOtherComprehensiveIncomeMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Accumulated Other Comprehensive(Loss) Income</link:label>
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    <link:label id="lab_us-gaap_EmployeeServiceShareBasedCompensationNonvestedAwardsTotalCompensationCostNotYetRecognized_label_en-US" xlink:label="lab_us-gaap_EmployeeServiceShareBasedCompensationNonvestedAwardsTotalCompensationCostNotYetRecognized" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Share-Based Payment Arrangement, Nonvested Award, Cost Not yet Recognized, Amount</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EmployeeServiceShareBasedCompensationNonvestedAwardsTotalCompensationCostNotYetRecognized" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_EmployeeServiceShareBasedCompensationNonvestedAwardsTotalCompensationCostNotYetRecognized"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EmployeeServiceShareBasedCompensationNonvestedAwardsTotalCompensationCostNotYetRecognized" xlink:to="lab_us-gaap_EmployeeServiceShareBasedCompensationNonvestedAwardsTotalCompensationCostNotYetRecognized" xlink:type="arc" order="1"/>
    <link:label id="lab_root_AmendedTermLoanCModificationMember_1eb47efb-fc04-473f-95e9-df2aed3c3414_terseLabel_en-US" xlink:label="lab_root_AmendedTermLoanCModificationMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Amended Term Loan C, Modification</link:label>
    <link:label id="lab_root_AmendedTermLoanCModificationMember_label_en-US" xlink:label="lab_root_AmendedTermLoanCModificationMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Amended Term Loan C, Modification [Member]</link:label>
    <link:label id="lab_root_AmendedTermLoanCModificationMember_documentation_en-US" xlink:label="lab_root_AmendedTermLoanCModificationMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Amended Term Loan C, Modification</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_root_AmendedTermLoanCModificationMember" xlink:href="root-20251231.xsd#root_AmendedTermLoanCModificationMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_root_AmendedTermLoanCModificationMember" xlink:to="lab_root_AmendedTermLoanCModificationMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ReinsuranceRecoverableCreditLossExpenseReversal_6aec50f3-daa0-4353-a607-a56821c90ab2_terseLabel_en-US" xlink:label="lab_us-gaap_ReinsuranceRecoverableCreditLossExpenseReversal" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Expense related to allowance for credit loss</link:label>
    <link:label id="lab_us-gaap_ReinsuranceRecoverableCreditLossExpenseReversal_label_en-US" xlink:label="lab_us-gaap_ReinsuranceRecoverableCreditLossExpenseReversal" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Reinsurance Recoverable, Credit Loss Expense (Reversal)</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ReinsuranceRecoverableCreditLossExpenseReversal" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_ReinsuranceRecoverableCreditLossExpenseReversal"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ReinsuranceRecoverableCreditLossExpenseReversal" xlink:to="lab_us-gaap_ReinsuranceRecoverableCreditLossExpenseReversal" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPositionLessThan12Months_366e5382-eec5-45b1-b4f2-8c8dffb3d20e_terseLabel_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPositionLessThan12Months" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Less than 12 Months</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" 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/2025/elts/us-gaap-2025.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_us-gaap_LongTermDebtFairValue_6e92384c-4daf-4aaa-94d2-4f1ae88ac3ec_terseLabel_en-US" xlink:label="lab_us-gaap_LongTermDebtFairValue" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2025/elts/us-gaap-2025.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_ecd_ChangedPeerGroupFnTextBlock_terseLabel_en-US" xlink:label="lab_ecd_ChangedPeerGroupFnTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Changed Peer Group, Footnote</link:label>
    <link:label id="lab_ecd_ChangedPeerGroupFnTextBlock_label_en-US" xlink:label="lab_ecd_ChangedPeerGroupFnTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Changed Peer Group, Footnote [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_ChangedPeerGroupFnTextBlock" xlink:href="https://xbrl.sec.gov/ecd/2025/ecd-2025.xsd#ecd_ChangedPeerGroupFnTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_ChangedPeerGroupFnTextBlock" xlink:to="lab_ecd_ChangedPeerGroupFnTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ShortDurationInsuranceContractAccidentYear2021Member_4af9a8d2-fe8c-49c7-9d51-05a4be193ad8_terseLabel_en-US" xlink:label="lab_us-gaap_ShortDurationInsuranceContractAccidentYear2021Member" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">2021</link:label>
    <link:label id="lab_us-gaap_ShortDurationInsuranceContractAccidentYear2021Member_label_en-US" xlink:label="lab_us-gaap_ShortDurationInsuranceContractAccidentYear2021Member" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Short-Duration Insurance Contract, Accident Year 2021 [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShortDurationInsuranceContractAccidentYear2021Member" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_ShortDurationInsuranceContractAccidentYear2021Member"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ShortDurationInsuranceContractAccidentYear2021Member" xlink:to="lab_us-gaap_ShortDurationInsuranceContractAccidentYear2021Member" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_RepurchaseAgreementCounterpartyNameDomain_7dd39059-a50a-42e0-8077-6a522a23a6fc_terseLabel_en-US" xlink:label="lab_srt_RepurchaseAgreementCounterpartyNameDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2025/elts/srt-2025.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_LesseeOperatingLeaseLiabilityPaymentsDueYearTwo_7b632a2d-2872-4449-a058-de19f526ceb2_terseLabel_en-US" xlink:label="lab_us-gaap_LesseeOperatingLeaseLiabilityPaymentsDueYearTwo" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">2027</link:label>
    <link:label id="lab_us-gaap_LesseeOperatingLeaseLiabilityPaymentsDueYearTwo_label_en-US" xlink:label="lab_us-gaap_LesseeOperatingLeaseLiabilityPaymentsDueYearTwo" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Lessee, Operating Lease, Liability, to be Paid, Year Two</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LesseeOperatingLeaseLiabilityPaymentsDueYearTwo" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_LesseeOperatingLeaseLiabilityPaymentsDueYearTwo"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LesseeOperatingLeaseLiabilityPaymentsDueYearTwo" xlink:to="lab_us-gaap_LesseeOperatingLeaseLiabilityPaymentsDueYearTwo" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_CondensedFinancialInformationOfParentCompanyOnlyDisclosureAbstract_label_en-US" xlink:label="lab_srt_CondensedFinancialInformationOfParentCompanyOnlyDisclosureAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Condensed Financial Information Disclosure [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_CondensedFinancialInformationOfParentCompanyOnlyDisclosureAbstract" xlink:href="https://xbrl.fasb.org/srt/2025/elts/srt-2025.xsd#srt_CondensedFinancialInformationOfParentCompanyOnlyDisclosureAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_CondensedFinancialInformationOfParentCompanyOnlyDisclosureAbstract" xlink:to="lab_srt_CondensedFinancialInformationOfParentCompanyOnlyDisclosureAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_AdjToPeoCompFnTextBlock_terseLabel_en-US" xlink:label="lab_ecd_AdjToPeoCompFnTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Adjustment To PEO Compensation, Footnote</link:label>
    <link:label id="lab_ecd_AdjToPeoCompFnTextBlock_label_en-US" xlink:label="lab_ecd_AdjToPeoCompFnTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Adjustment To PEO Compensation, Footnote [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_AdjToPeoCompFnTextBlock" xlink:href="https://xbrl.sec.gov/ecd/2025/ecd-2025.xsd#ecd_AdjToPeoCompFnTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_AdjToPeoCompFnTextBlock" xlink:to="lab_ecd_AdjToPeoCompFnTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_SharebasedCompensationArrangementBySharebasedPaymentAwardOptionsOutstandingWeightedAverageRemainingContractualTerm2_f9571c67-9433-4ac3-b643-06e5270f8d79_terseLabel_en-US" xlink:label="lab_us-gaap_SharebasedCompensationArrangementBySharebasedPaymentAwardOptionsOutstandingWeightedAverageRemainingContractualTerm2" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2025/elts/us-gaap-2025.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_root_ClassOfWarrantOrRightNumberOfTranches_c63060ba-3564-4113-9f83-0cb6d419fc01_terseLabel_en-US" xlink:label="lab_root_ClassOfWarrantOrRightNumberOfTranches" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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" 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-20251231.xsd#root_ClassOfWarrantOrRightNumberOfTranches"/>
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    <link:label id="lab_us-gaap_ValuationAllowancesAndReservesTypeAxis_0080ed34-c5c4-4108-a6db-1a15b6068ad7_terseLabel_en-US" xlink:label="lab_us-gaap_ValuationAllowancesAndReservesTypeAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">SEC Schedule, 12-09, Valuation Allowances and Reserves Type [Axis]</link:label>
    <link:label id="lab_us-gaap_ValuationAllowancesAndReservesTypeAxis_label_en-US" xlink:label="lab_us-gaap_ValuationAllowancesAndReservesTypeAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">SEC Schedule, 12-09, Valuation Allowances and Reserves Type [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ValuationAllowancesAndReservesTypeAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_ValuationAllowancesAndReservesTypeAxis"/>
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    <link:label id="lab_us-gaap_InvestmentTypeAxis_d447efb0-c7d2-4c27-a4ed-3a165f77cd30_terseLabel_en-US" xlink:label="lab_us-gaap_InvestmentTypeAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2025/elts/us-gaap-2025.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_Investments_4f071e13-c875-47a9-8c1e-e4fadafc3a66_totalLabel_en-US" xlink:label="lab_us-gaap_Investments" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" 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" 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/2025/elts/us-gaap-2025.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_ecd_TrdArrIndTitle_terseLabel_en-US" xlink:label="lab_ecd_TrdArrIndTitle" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Title</link:label>
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    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_TrdArrIndTitle" xlink:to="lab_ecd_TrdArrIndTitle" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_PeerGroupTotalShareholderRtnAmt_terseLabel_en-US" xlink:label="lab_ecd_PeerGroupTotalShareholderRtnAmt" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Peer Group Total Shareholder Return Amount</link:label>
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    <link:loc xlink:type="locator" xlink:label="loc_ecd_PeerGroupTotalShareholderRtnAmt" xlink:href="https://xbrl.sec.gov/ecd/2025/ecd-2025.xsd#ecd_PeerGroupTotalShareholderRtnAmt"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_PeerGroupTotalShareholderRtnAmt" xlink:to="lab_ecd_PeerGroupTotalShareholderRtnAmt" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_CondensedStatementOfIncomeCaptionsLineItems_1d38efd8-56cb-40a7-9d2a-dcb267870253_terseLabel_en-US" xlink:label="lab_srt_CondensedStatementOfIncomeCaptionsLineItems" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Condensed Statement of Income Captions [Line Items]</link:label>
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    <link:loc xlink:type="locator" xlink:label="loc_srt_CondensedStatementOfIncomeCaptionsLineItems" xlink:href="https://xbrl.fasb.org/srt/2025/elts/srt-2025.xsd#srt_CondensedStatementOfIncomeCaptionsLineItems"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_CondensedStatementOfIncomeCaptionsLineItems" xlink:to="lab_srt_CondensedStatementOfIncomeCaptionsLineItems" xlink:type="arc" order="1"/>
    <link:label id="lab_root_JonathanAllisonMember_label_en-US" xlink:label="lab_root_JonathanAllisonMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Jonathan Allison [Member]</link:label>
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    <link:loc xlink:type="locator" xlink:label="loc_ecd_NonPeoNeoMember" xlink:href="https://xbrl.sec.gov/ecd/2025/ecd-2025.xsd#ecd_NonPeoNeoMember"/>
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    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardOptionsOutstandingIntrinsicValue_e4a71ff3-d63e-45c3-aa67-a854ef2cdc51_terseLabel_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardOptionsOutstandingIntrinsicValue" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Outstanding, aggregate intrinsic value</link:label>
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    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardOptionsOutstandingIntrinsicValue" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardOptionsOutstandingIntrinsicValue"/>
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    <link:label id="lab_us-gaap_PurchaseObligationFiscalYearMaturityAbstract_8c76afb6-61ae-42d4-805d-83c332ebee58_terseLabel_en-US" xlink:label="lab_us-gaap_PurchaseObligationFiscalYearMaturityAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Purchase Obligations</link:label>
    <link:label id="lab_us-gaap_PurchaseObligationFiscalYearMaturityAbstract_label_en-US" xlink:label="lab_us-gaap_PurchaseObligationFiscalYearMaturityAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Purchase Obligation, Fiscal Year Maturity [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PurchaseObligationFiscalYearMaturityAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_PurchaseObligationFiscalYearMaturityAbstract"/>
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    <link:label id="lab_us-gaap_ShortdurationInsuranceContractsReconciliationOfClaimsDevelopmentToLiabilityTableTextBlock_f3940ee1-6573-4183-b787-88b2aa5e2171_terseLabel_en-US" xlink:label="lab_us-gaap_ShortdurationInsuranceContractsReconciliationOfClaimsDevelopmentToLiabilityTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Schedule of Reconciliation of Claims Development to Liability</link:label>
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    <link:label id="lab_us-gaap_PreferredStockDividendRatePercentage_e83a6150-2ff7-4a6a-a009-4d6fe9de08d3_terseLabel_en-US" xlink:label="lab_us-gaap_PreferredStockDividendRatePercentage" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Preferred stock, dividend percentage</link:label>
    <link:label id="lab_us-gaap_PreferredStockDividendRatePercentage_label_en-US" xlink:label="lab_us-gaap_PreferredStockDividendRatePercentage" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Preferred Stock, Dividend Rate, Percentage</link:label>
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    <link:label id="lab_us-gaap_SubsidiarySaleOfStockAxis_f9ddb1f7-b45c-456d-b24f-ab05272895d7_terseLabel_en-US" xlink:label="lab_us-gaap_SubsidiarySaleOfStockAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Sale of Stock [Axis]</link:label>
    <link:label id="lab_us-gaap_SubsidiarySaleOfStockAxis_label_en-US" xlink:label="lab_us-gaap_SubsidiarySaleOfStockAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Sale of Stock [Axis]</link:label>
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    <link:label id="lab_us-gaap_AllowanceForReinsuranceRecoverableMember_974eff7e-76ed-40b8-88f3-a0ba5254906e_terseLabel_en-US" xlink:label="lab_us-gaap_AllowanceForReinsuranceRecoverableMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Allowance for reinsurance recoverables</link:label>
    <link:label id="lab_us-gaap_AllowanceForReinsuranceRecoverableMember_label_en-US" xlink:label="lab_us-gaap_AllowanceForReinsuranceRecoverableMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">SEC Schedule, 12-09, Allowance, Reinsurance Recoverable [Member]</link:label>
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    <link:label id="lab_us-gaap_AvailableForSaleDebtSecuritiesAccumulatedGrossUnrealizedGainBeforeTax_8650bc8a-842f-45b3-a294-264a74b4db50_terseLabel_en-US" xlink:label="lab_us-gaap_AvailableForSaleDebtSecuritiesAccumulatedGrossUnrealizedGainBeforeTax" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Gross Unrealized Gains</link:label>
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    <link:label id="lab_us-gaap_LesseeOperatingLeaseLiabilityPaymentsDueNextTwelveMonths_c5c2ce8c-f11f-4a77-abf4-f2916ed3963f_terseLabel_en-US" xlink:label="lab_us-gaap_LesseeOperatingLeaseLiabilityPaymentsDueNextTwelveMonths" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">2026</link:label>
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    <link:label id="lab_us-gaap_AllowanceForUncollectiblePremiumsReceivableMember_6eb3e8de-c14f-421a-abb2-957cd4a2f793_terseLabel_en-US" xlink:label="lab_us-gaap_AllowanceForUncollectiblePremiumsReceivableMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Allowance for premium receivables</link:label>
    <link:label id="lab_us-gaap_AllowanceForUncollectiblePremiumsReceivableMember_label_en-US" xlink:label="lab_us-gaap_AllowanceForUncollectiblePremiumsReceivableMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">SEC Schedule, 12-09, Allowance, Uncollectible Premium Receivable [Member]</link:label>
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    <link:label id="lab_us-gaap_LeaseholdImprovementsMember_5e9156c0-e83d-4476-a995-396dd873bebf_terseLabel_en-US" xlink:label="lab_us-gaap_LeaseholdImprovementsMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Leasehold improvements</link:label>
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    <link:label id="lab_us-gaap_DeferredIncomeTaxExpenseBenefitContinuingOperationsAbstract_838c6abc-c63d-4753-8727-7e98f8a7cd6a_terseLabel_en-US" xlink:label="lab_us-gaap_DeferredIncomeTaxExpenseBenefitContinuingOperationsAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Deferred:</link:label>
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    <link:label id="lab_us-gaap_ScheduleOfLiabilityForUnpaidClaimsAndClaimsAdjustmentExpense_6999adaa-79f8-4dd0-ab66-259fd1cc9474_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfLiabilityForUnpaidClaimsAndClaimsAdjustmentExpense" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Schedule of Reserve Balance</link:label>
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    <link:label id="lab_us-gaap_EstimateOfFairValueFairValueDisclosureMember_f08a1318-c712-468b-8593-f1759967919d_terseLabel_en-US" xlink:label="lab_us-gaap_EstimateOfFairValueFairValueDisclosureMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2025/elts/us-gaap-2025.xsd#us-gaap_EstimateOfFairValueFairValueDisclosureMember"/>
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    <link:label id="lab_root_CommutationOfCertainAgreementsMember_d22a2414-7ecd-4e95-bec0-541e72f80b83_terseLabel_en-US" xlink:label="lab_root_CommutationOfCertainAgreementsMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Commutation of Certain Agreements</link:label>
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    <link:label id="lab_root_CommutationOfCertainAgreementsMember_documentation_en-US" xlink:label="lab_root_CommutationOfCertainAgreementsMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Commutation of Certain Agreements</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_root_CommutationOfCertainAgreementsMember" xlink:href="root-20251231.xsd#root_CommutationOfCertainAgreementsMember"/>
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    <link:label id="lab_root_CommonStockVotingRightsVotes_8cb4e8d4-5467-4c8c-87ad-54c75cc335a9_terseLabel_en-US" xlink:label="lab_root_CommonStockVotingRightsVotes" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Voting rights</link:label>
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    <link:label id="lab_root_CommonStockVotingRightsVotes_documentation_en-US" xlink:label="lab_root_CommonStockVotingRightsVotes" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Common Stock, Voting Rights, Votes</link:label>
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    <link:label id="lab_us-gaap_ValuationAllowancesAndReservesChargedToCostAndExpense_ae05b2c1-9210-4a55-9562-b7e738184b42_terseLabel_en-US" xlink:label="lab_us-gaap_ValuationAllowancesAndReservesChargedToCostAndExpense" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Charged to costs and expenses</link:label>
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    <link:label id="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterOneThroughFiveYearsAmortizedCost_53661c7c-9b83-4659-a49b-96acd1176a1b_verboseLabel_en-US" xlink:label="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterOneThroughFiveYearsAmortizedCost" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Due after one year through five years</link:label>
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    <link:label id="lab_root_DebtSecuritiesAvailableForSaleMember_2760d537-c404-408a-b63e-fcbc824a4f0e_terseLabel_en-US" xlink:label="lab_root_DebtSecuritiesAvailableForSaleMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">AFS Securities</link:label>
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    <link:label id="lab_us-gaap_WeightedAverageNumberOfSharesOutstandingDilutedDisclosureItemsAbstract_88ae42ac-cbac-44de-9851-071da990fe94_terseLabel_en-US" xlink:label="lab_us-gaap_WeightedAverageNumberOfSharesOutstandingDilutedDisclosureItemsAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Denominator:</link:label>
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    <link:label id="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterFiveThroughTenYearsAmortizedCost_da719f6f-9239-4ad4-8dd0-e0de42f00a72_verboseLabel_en-US" xlink:label="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterFiveThroughTenYearsAmortizedCost" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Due five years through 10 years</link:label>
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    <link:label id="lab_us-gaap_AccumulatedOtherComprehensiveIncomeLossNetOfTax_67c74ce7-1bfa-49f5-bc11-6eee6be963e0_terseLabel_en-US" xlink:label="lab_us-gaap_AccumulatedOtherComprehensiveIncomeLossNetOfTax" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Accumulated other comprehensive income (loss)</link:label>
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    <link:label id="lab_us-gaap_SellingAndMarketingExpense_413a5add-4c34-4565-a5d8-0f3a11d01bc0_terseLabel_en-US" xlink:label="lab_us-gaap_SellingAndMarketingExpense" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Sales and marketing</link:label>
    <link:label id="lab_us-gaap_SellingAndMarketingExpense_1aa643d9-86d6-4c57-bc8d-37fbefeb78de_verboseLabel_en-US" xlink:label="lab_us-gaap_SellingAndMarketingExpense" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" 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" 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_TransfersAndServicingOfFinancialInstrumentsTypesOfFinancialInstrumentsDomain_a3384ed2-a767-4a50-8327-c147c9cbafda_terseLabel_en-US" xlink:label="lab_us-gaap_TransfersAndServicingOfFinancialInstrumentsTypesOfFinancialInstrumentsDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2025/elts/us-gaap-2025.xsd#us-gaap_TransfersAndServicingOfFinancialInstrumentsTypesOfFinancialInstrumentsDomain"/>
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    <link:label id="lab_us-gaap_DeferredIncomeTaxLiabilities_eb3cf493-bde9-4553-a04d-e623cb8fc3e6_totalLabel_en-US" xlink:label="lab_us-gaap_DeferredIncomeTaxLiabilities" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Deferred tax liabilities</link:label>
    <link:label id="lab_us-gaap_DeferredIncomeTaxLiabilities_label_en-US" xlink:label="lab_us-gaap_DeferredIncomeTaxLiabilities" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Deferred Tax Liabilities, Gross</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DeferredIncomeTaxLiabilities" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_DeferredIncomeTaxLiabilities"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DeferredIncomeTaxLiabilities" xlink:to="lab_us-gaap_DeferredIncomeTaxLiabilities" xlink:type="arc" order="1"/>
    <link:label id="lab_root_TaxCreditCarryforwardNotSubjectToExpiration_e4d5d5b1-2c01-4708-9a71-f01b1634c631_terseLabel_en-US" xlink:label="lab_root_TaxCreditCarryforwardNotSubjectToExpiration" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Carryforward indefinitely</link:label>
    <link:label id="lab_root_TaxCreditCarryforwardNotSubjectToExpiration_label_en-US" xlink:label="lab_root_TaxCreditCarryforwardNotSubjectToExpiration" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Tax Credit Carryforward, Not Subject To Expiration</link:label>
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    <link:label id="lab_ecd_AggtPnsnAdjsSvcCstMember_terseLabel_en-US" xlink:label="lab_ecd_AggtPnsnAdjsSvcCstMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Aggregate Pension Adjustments Service Cost</link:label>
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    <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" 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" xml:lang="en-US">Other Insurance Expense (Income)</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_root_OtherInsuranceExpenseIncome" xlink:href="root-20251231.xsd#root_OtherInsuranceExpenseIncome"/>
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    <link:label id="lab_us-gaap_IncomeTaxReconciliationNondeductibleExpenseOther_1b1008a5-646a-4967-a07f-9da691a69b7b_terseLabel_en-US" xlink:label="lab_us-gaap_IncomeTaxReconciliationNondeductibleExpenseOther" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Other nondeductible expenses</link:label>
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    <link:label id="lab_us-gaap_ScheduleOfInvestmentIncomeReportedAmountsByCategoryLineItems_30d7f2ef-c8ee-49c8-a1ed-9b403ef7f1a7_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfInvestmentIncomeReportedAmountsByCategoryLineItems" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Net Investment Income [Line Items]</link:label>
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    <link:label id="lab_us-gaap_PreferredStockConvertibleConversionPrice_1e6bf1f3-cdd7-4f55-887d-b16876b626e7_terseLabel_en-US" xlink:label="lab_us-gaap_PreferredStockConvertibleConversionPrice" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Conversion price (in dollars per share)</link:label>
    <link:label id="lab_us-gaap_PreferredStockConvertibleConversionPrice_label_en-US" xlink:label="lab_us-gaap_PreferredStockConvertibleConversionPrice" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Preferred Stock, Convertible, Conversion Price</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PreferredStockConvertibleConversionPrice" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_PreferredStockConvertibleConversionPrice"/>
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    <link:label id="lab_us-gaap_IncomeTaxDisclosureAbstract_5420673f-c7ec-45ef-b90e-bb9f54231508_terseLabel_en-US" xlink:label="lab_us-gaap_IncomeTaxDisclosureAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2025/elts/us-gaap-2025.xsd#us-gaap_IncomeTaxDisclosureAbstract"/>
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    <link:label id="lab_root_OperatingLossCarryforwardsSubjectToExpiration_84454846-2e63-411b-bb70-445a2bf4f896_terseLabel_en-US" xlink:label="lab_root_OperatingLossCarryforwardsSubjectToExpiration" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Carryforward with Expiration</link:label>
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    <link:label id="lab_root_OperatingLossCarryforwardsSubjectToExpiration_documentation_en-US" xlink:label="lab_root_OperatingLossCarryforwardsSubjectToExpiration" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Operating Loss Carryforwards, Subject to Expiration</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_root_OperatingLossCarryforwardsSubjectToExpiration" xlink:href="root-20251231.xsd#root_OperatingLossCarryforwardsSubjectToExpiration"/>
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    <link:label id="lab_us-gaap_PurchaseObligationDueInFourthYear_cef08fac-2336-489e-baa3-dc04836f4055_terseLabel_en-US" xlink:label="lab_us-gaap_PurchaseObligationDueInFourthYear" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">2029</link:label>
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    <link:label id="lab_us-gaap_PreferredStockSharesOutstanding_594ce4aa-b2bf-454a-9740-4b421d3fc571_terseLabel_en-US" xlink:label="lab_us-gaap_PreferredStockSharesOutstanding" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Preferred stock, 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" 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/2025/elts/us-gaap-2025.xsd#us-gaap_PreferredStockSharesOutstanding"/>
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    <link:label id="lab_us-gaap_CurrentStateAndLocalTaxExpenseBenefit_label_en-US" xlink:label="lab_us-gaap_CurrentStateAndLocalTaxExpenseBenefit" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Current State and Local Tax Expense (Benefit)</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CurrentStateAndLocalTaxExpenseBenefit" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_CurrentStateAndLocalTaxExpenseBenefit"/>
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    <link:label id="lab_root_OperatingLossAndTaxCreditCarryforwardsSubjectToExpiration_8d513f84-5fd2-4e0a-a595-5f188d76ce42_totalLabel_en-US" xlink:label="lab_root_OperatingLossAndTaxCreditCarryforwardsSubjectToExpiration" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Operating loss and tax credit carryforwards, subject to expiration</link:label>
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    <link:label id="lab_root_OperatingLossAndTaxCreditCarryforwardsSubjectToExpiration_documentation_en-US" xlink:label="lab_root_OperatingLossAndTaxCreditCarryforwardsSubjectToExpiration" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Operating Loss And Tax Credit Carryforwards, Subject to Expiration</link:label>
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    <link:label id="lab_us-gaap_OperatingLeaseRightOfUseAssetStatementOfFinancialPositionExtensibleList_297aaf08-126f-405f-a4c3-a45c2e61f506_terseLabel_en-US" xlink:label="lab_us-gaap_OperatingLeaseRightOfUseAssetStatementOfFinancialPositionExtensibleList" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Operating lease, right-of-use asset, statement of financial position [Extensible Enumeration]</link:label>
    <link:label id="lab_us-gaap_OperatingLeaseRightOfUseAssetStatementOfFinancialPositionExtensibleList_label_en-US" xlink:label="lab_us-gaap_OperatingLeaseRightOfUseAssetStatementOfFinancialPositionExtensibleList" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Operating Lease, Right-of-Use Asset, Statement of Financial Position [Extensible Enumeration]</link:label>
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    <link:label id="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterOneThroughFiveYearsFairValue_6800c24e-bf38-4b54-81aa-f5da2112bd75_verboseLabel_en-US" xlink:label="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterOneThroughFiveYearsFairValue" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Due after one year through five years</link:label>
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    <link:label id="lab_us-gaap_SummaryOfTaxCreditCarryforwardsTextBlock_88e87507-1d9c-4ffb-9a36-5ad9dddcdd50_terseLabel_en-US" xlink:label="lab_us-gaap_SummaryOfTaxCreditCarryforwardsTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Schedule of Tax Credit Carryforwards</link:label>
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    <link:label id="lab_dei_DocumentPeriodEndDate_59f03feb-7b26-4fa9-a59f-d7ab58aef74d_terseLabel_en-US" xlink:label="lab_dei_DocumentPeriodEndDate" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Document Period End Date</link:label>
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    <link:label id="lab_us-gaap_IncomeTaxDisclosureTextBlock_517dcc06-c15d-4bfd-b99d-20afdb75155c_terseLabel_en-US" xlink:label="lab_us-gaap_IncomeTaxDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">INCOME TAXES</link:label>
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    <link:label id="lab_us-gaap_CommonClassAMember_408919c4-8eae-4213-9e17-e4cb7bd31fa1_terseLabel_en-US" xlink:label="lab_us-gaap_CommonClassAMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Class A Shares</link:label>
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    <link:label id="lab_us-gaap_CapitalizationOfDeferredPolicyAcquisitionCostsPolicy_d50d564c-ddb0-4060-bf43-32c185aa494c_terseLabel_en-US" xlink:label="lab_us-gaap_CapitalizationOfDeferredPolicyAcquisitionCostsPolicy" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Deferred Policy Acquisition Costs</link:label>
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    <link:label id="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterFiveThroughTenYearsFairValue_9a97658d-7360-4c49-b6bc-822af29bbc76_verboseLabel_en-US" xlink:label="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterFiveThroughTenYearsFairValue" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Due five years through 10 years</link:label>
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    <link:label id="lab_us-gaap_TaxCreditCarryforwardAxis_351e28f7-9c41-4690-b847-c845ba8d0c2c_terseLabel_en-US" xlink:label="lab_us-gaap_TaxCreditCarryforwardAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Tax Credit Carryforward [Axis]</link:label>
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    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EffectiveIncomeTaxRateReconciliationNondeductibleExpenseOther" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_EffectiveIncomeTaxRateReconciliationNondeductibleExpenseOther"/>
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    <link:label id="lab_us-gaap_DebtInstrumentCarryingAmount_54a53e62-ed8e-4553-a879-3ff271ebb2b5_terseLabel_en-US" xlink:label="lab_us-gaap_DebtInstrumentCarryingAmount" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Principal balance</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" 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/2025/elts/us-gaap-2025.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_ShareBasedCompensationArrangementsByShareBasedPaymentAwardOptionsGrantsInPeriodWeightedAverageExercisePrice_09ad2c9d-8dbb-4e48-8bea-cedbc1ada9d8_terseLabel_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementsByShareBasedPaymentAwardOptionsGrantsInPeriodWeightedAverageExercisePrice" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Granted (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" 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/2025/elts/us-gaap-2025.xsd#us-gaap_ShareBasedCompensationArrangementsByShareBasedPaymentAwardOptionsGrantsInPeriodWeightedAverageExercisePrice"/>
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    <link:label id="lab_dei_EntityWellKnownSeasonedIssuer_bfdd2436-f083-4821-9486-eb07cfaa368d_terseLabel_en-US" xlink:label="lab_dei_EntityWellKnownSeasonedIssuer" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Entity Well-known Seasoned Issuer</link:label>
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    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_EntityWellKnownSeasonedIssuer" xlink:to="lab_dei_EntityWellKnownSeasonedIssuer" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LesseeOperatingLeaseLiabilityPaymentsDue_bb33bae9-f967-4c2a-b444-6d6a54afad0e_totalLabel_en-US" xlink:label="lab_us-gaap_LesseeOperatingLeaseLiabilityPaymentsDue" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Total future lease payments</link:label>
    <link:label id="lab_us-gaap_LesseeOperatingLeaseLiabilityPaymentsDue_label_en-US" xlink:label="lab_us-gaap_LesseeOperatingLeaseLiabilityPaymentsDue" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Lessee, Operating Lease, Liability, to be Paid</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LesseeOperatingLeaseLiabilityPaymentsDue" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_LesseeOperatingLeaseLiabilityPaymentsDue"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LesseeOperatingLeaseLiabilityPaymentsDue" xlink:to="lab_us-gaap_LesseeOperatingLeaseLiabilityPaymentsDue" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_OtherComprehensiveIncomeUnrealizedHoldingGainLossOnSecuritiesArisingDuringPeriodNetOfTax_ff9fa473-6a90-4ac9-99ae-64e5afbac431_terseLabel_en-US" xlink:label="lab_us-gaap_OtherComprehensiveIncomeUnrealizedHoldingGainLossOnSecuritiesArisingDuringPeriodNetOfTax" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Changes in net unrealized gains 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" 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/2025/elts/us-gaap-2025.xsd#us-gaap_OtherComprehensiveIncomeUnrealizedHoldingGainLossOnSecuritiesArisingDuringPeriodNetOfTax"/>
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    <link:label id="lab_us-gaap_ShortDurationInsuranceContractAccidentYear2024Member_9a8926c4-57c1-4fbd-bb71-32f831774393_terseLabel_en-US" xlink:label="lab_us-gaap_ShortDurationInsuranceContractAccidentYear2024Member" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">2024</link:label>
    <link:label id="lab_us-gaap_ShortDurationInsuranceContractAccidentYear2024Member_label_en-US" xlink:label="lab_us-gaap_ShortDurationInsuranceContractAccidentYear2024Member" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Short-Duration Insurance Contract, Accident Year 2024 [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShortDurationInsuranceContractAccidentYear2024Member" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_ShortDurationInsuranceContractAccidentYear2024Member"/>
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    <link:label id="lab_root_RegulatoryAssetRequirementSpecialDepositsFairValue_8f601ee4-f42c-479c-aeed-7d9fb4aa11e0_terseLabel_en-US" xlink:label="lab_root_RegulatoryAssetRequirementSpecialDepositsFairValue" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Fair of special deposits</link:label>
    <link:label id="lab_root_RegulatoryAssetRequirementSpecialDepositsFairValue_label_en-US" xlink:label="lab_root_RegulatoryAssetRequirementSpecialDepositsFairValue" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Regulatory Asset Requirement, Special Deposits, Fair Value</link:label>
    <link:label id="lab_root_RegulatoryAssetRequirementSpecialDepositsFairValue_documentation_en-US" xlink:label="lab_root_RegulatoryAssetRequirementSpecialDepositsFairValue" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Regulatory Asset Requirement, Special Deposits, Fair Value</link:label>
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    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleUnrealizedLossPositionFairValueTableTextBlock_8af109da-1713-4148-bb96-5a9d614062a7_terseLabel_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleUnrealizedLossPositionFairValueTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2025/elts/us-gaap-2025.xsd#us-gaap_DebtSecuritiesAvailableForSaleUnrealizedLossPositionFairValueTableTextBlock"/>
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    <link:label id="lab_ecd_TrdArrExpirationDate_terseLabel_en-US" xlink:label="lab_ecd_TrdArrExpirationDate" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Expiration Date</link:label>
    <link:label id="lab_ecd_TrdArrExpirationDate_label_en-US" xlink:label="lab_ecd_TrdArrExpirationDate" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Trading Arrangement Expiration Date</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_TrdArrExpirationDate" xlink:href="https://xbrl.sec.gov/ecd/2025/ecd-2025.xsd#ecd_TrdArrExpirationDate"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_TrdArrExpirationDate" xlink:to="lab_ecd_TrdArrExpirationDate" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_IncreaseDecreaseInOtherOperatingLiabilities_039387a3-44d7-43c6-ab71-2a2bc3c4ed03_terseLabel_en-US" xlink:label="lab_us-gaap_IncreaseDecreaseInOtherOperatingLiabilities" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2025/elts/us-gaap-2025.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_PropertyPlantAndEquipmentNet_c51c841a-2425-4636-bb44-aef2a49ed473_totalLabel_en-US" xlink:label="lab_us-gaap_PropertyPlantAndEquipmentNet" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Fixed assets, net</link:label>
    <link:label id="lab_us-gaap_PropertyPlantAndEquipmentNet_label_en-US" xlink:label="lab_us-gaap_PropertyPlantAndEquipmentNet" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Property, Plant and Equipment, Net</link:label>
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    <link:label id="lab_us-gaap_RestructuringCharges_ca716e5c-075f-4cd7-8db4-ca52b4e019d5_verboseLabel_en-US" xlink:label="lab_us-gaap_RestructuringCharges" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Expense incurred</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" xml:lang="en-US">Restructuring Charges</link:label>
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    <link:label id="lab_root_A2020EmployeeStockPurchasePlanMember_2e9ba06f-4d13-4db1-92d3-a1c4b4729afb_terseLabel_en-US" xlink:label="lab_root_A2020EmployeeStockPurchasePlanMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">2020 ESPP</link:label>
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    <link:label id="lab_root_A2020EmployeeStockPurchasePlanMember_documentation_en-US" xlink:label="lab_root_A2020EmployeeStockPurchasePlanMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">2020 Employee Stock Purchase Plan</link:label>
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    <link:label id="lab_ecd_MeasureAxis_terseLabel_en-US" xlink:label="lab_ecd_MeasureAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Measure:</link:label>
    <link:label id="lab_ecd_MeasureAxis_label_en-US" xlink:label="lab_ecd_MeasureAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Measure [Axis]</link:label>
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    <link:label id="lab_root_UnearnedPremiumsNetAbstract_9b0b6c18-47c1-4590-bbb2-5214ae34f1be_terseLabel_en-US" xlink:label="lab_root_UnearnedPremiumsNetAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Unearned premiums:</link:label>
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    <link:label id="lab_root_UnearnedPremiumsNetAbstract_documentation_en-US" xlink:label="lab_root_UnearnedPremiumsNetAbstract" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Unearned Premiums, Net</link:label>
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    <link:label id="lab_us-gaap_ValuationTechniqueAxis_4d2f9a2b-03c5-4ac9-b434-66f5af704695_terseLabel_en-US" xlink:label="lab_us-gaap_ValuationTechniqueAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Valuation Approach and Technique [Axis]</link:label>
    <link:label id="lab_us-gaap_ValuationTechniqueAxis_label_en-US" xlink:label="lab_us-gaap_ValuationTechniqueAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Valuation Approach and Technique [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ValuationTechniqueAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_ValuationTechniqueAxis"/>
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    <link:label id="lab_us-gaap_ScheduleOfStockholdersEquityNoteWarrantsOrRightsTextBlock_923dab9b-27fa-4b2c-8db8-4d9cf68f373e_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfStockholdersEquityNoteWarrantsOrRightsTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Schedule of Warrants</link:label>
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    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfStockholdersEquityNoteWarrantsOrRightsTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_ScheduleOfStockholdersEquityNoteWarrantsOrRightsTextBlock"/>
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    <link:label id="lab_us-gaap_PropertyPlantAndEquipmentTypeDomain_efdcf5f8-b708-4e94-a9b9-34493f633045_terseLabel_en-US" xlink:label="lab_us-gaap_PropertyPlantAndEquipmentTypeDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Long-Lived Tangible Asset [Domain]</link:label>
    <link:label id="lab_us-gaap_PropertyPlantAndEquipmentTypeDomain_label_en-US" xlink:label="lab_us-gaap_PropertyPlantAndEquipmentTypeDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Long-Lived Tangible Asset [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PropertyPlantAndEquipmentTypeDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_PropertyPlantAndEquipmentTypeDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PropertyPlantAndEquipmentTypeDomain" xlink:to="lab_us-gaap_PropertyPlantAndEquipmentTypeDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_StatutoryAccountingPracticesStatutoryCapitalAndSurplusBalance_c374307d-0a80-4b95-8a29-2f7b8e38a999_terseLabel_en-US" xlink:label="lab_us-gaap_StatutoryAccountingPracticesStatutoryCapitalAndSurplusBalance" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Statutory Capital and Surplus</link:label>
    <link:label id="lab_us-gaap_StatutoryAccountingPracticesStatutoryCapitalAndSurplusBalance_label_en-US" xlink:label="lab_us-gaap_StatutoryAccountingPracticesStatutoryCapitalAndSurplusBalance" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Statutory Accounting Practices, Statutory Capital and Surplus, Balance</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_StatutoryAccountingPracticesStatutoryCapitalAndSurplusBalance" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_StatutoryAccountingPracticesStatutoryCapitalAndSurplusBalance"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_StatutoryAccountingPracticesStatutoryCapitalAndSurplusBalance" xlink:to="lab_us-gaap_StatutoryAccountingPracticesStatutoryCapitalAndSurplusBalance" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_PvpTableTextBlock_terseLabel_en-US" xlink:label="lab_ecd_PvpTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Pay vs Performance Disclosure, Table</link:label>
    <link:label id="lab_ecd_PvpTableTextBlock_label_en-US" xlink:label="lab_ecd_PvpTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Pay vs Performance [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_PvpTableTextBlock" xlink:href="https://xbrl.sec.gov/ecd/2025/ecd-2025.xsd#ecd_PvpTableTextBlock"/>
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    <link:label id="lab_ecd_ForgoneRecoveryDueToViolationOfHomeCountryLawAmt_terseLabel_en-US" xlink:label="lab_ecd_ForgoneRecoveryDueToViolationOfHomeCountryLawAmt" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Forgone Recovery due to Violation of Home Country Law, Amount</link:label>
    <link:label id="lab_ecd_ForgoneRecoveryDueToViolationOfHomeCountryLawAmt_label_en-US" xlink:label="lab_ecd_ForgoneRecoveryDueToViolationOfHomeCountryLawAmt" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Forgone Recovery due to Violation of Home Country Law, Amount</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_ForgoneRecoveryDueToViolationOfHomeCountryLawAmt" xlink:href="https://xbrl.sec.gov/ecd/2025/ecd-2025.xsd#ecd_ForgoneRecoveryDueToViolationOfHomeCountryLawAmt"/>
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    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardFairValueAssumptionsRiskFreeInterestRate_3deb2db6-b8ec-4034-a61a-b1a1a9598295_terseLabel_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardFairValueAssumptionsRiskFreeInterestRate" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Risk free interest rate</link:label>
    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardFairValueAssumptionsRiskFreeInterestRate_label_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardFairValueAssumptionsRiskFreeInterestRate" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Share-Based Compensation Arrangement by Share-Based Payment Award, Fair Value Assumptions, Risk Free Interest Rate</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardFairValueAssumptionsRiskFreeInterestRate" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardFairValueAssumptionsRiskFreeInterestRate"/>
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    <link:label id="lab_us-gaap_InvestmentIncomeInvestmentExpense_5ad36538-5fb9-4114-a26b-35214ad8fb94_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_InvestmentIncomeInvestmentExpense" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" 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" 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/2025/elts/us-gaap-2025.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_dei_EntityTaxIdentificationNumber_c22a501a-0f77-4e90-a2fe-6e574ef75277_terseLabel_en-US" xlink:label="lab_dei_EntityTaxIdentificationNumber" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" xml:lang="en-US">Entity Tax Identification Number</link:label>
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    <link:label id="lab_us-gaap_AssetAcquisitionAxis_1aaada10-3514-423d-b3c7-ba7e2e5150b8_terseLabel_en-US" xlink:label="lab_us-gaap_AssetAcquisitionAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Asset Acquisition [Axis]</link:label>
    <link:label id="lab_us-gaap_AssetAcquisitionAxis_label_en-US" xlink:label="lab_us-gaap_AssetAcquisitionAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Asset Acquisition [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AssetAcquisitionAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_AssetAcquisitionAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AssetAcquisitionAxis" xlink:to="lab_us-gaap_AssetAcquisitionAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardOptionsOutstandingWeightedAverageExercisePrice_39424f21-b64e-4139-ab9e-755ff86fde4b_periodStartLabel_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardOptionsOutstandingWeightedAverageExercisePrice" xlink:role="http://www.xbrl.org/2003/role/periodStartLabel" xlink:type="resource" xml:lang="en-US">Outstanding, beginning balance (in dollars per share)</link:label>
    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardOptionsOutstandingWeightedAverageExercisePrice_93d69d39-7e89-4fe1-b07b-7be5f8e40a2f_periodEndLabel_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardOptionsOutstandingWeightedAverageExercisePrice" xlink:role="http://www.xbrl.org/2003/role/periodEndLabel" xlink:type="resource" xml:lang="en-US">Outstanding, ending balance (in dollars per share)</link:label>
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    <link:label id="lab_us-gaap_CommonStockSharesIssued_2d374395-589e-4a41-9d33-128190d2856c_terseLabel_en-US" xlink:label="lab_us-gaap_CommonStockSharesIssued" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" xml:lang="en-US">Common Stock, Shares, Issued</link:label>
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    <link:label id="lab_us-gaap_OperatingLeaseWeightedAverageRemainingLeaseTerm1_7629ab22-42ef-42f9-affa-df4a7bba3854_terseLabel_en-US" xlink:label="lab_us-gaap_OperatingLeaseWeightedAverageRemainingLeaseTerm1" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Weighted-average of remaining operating lease term (years)</link:label>
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    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OperatingLeaseWeightedAverageRemainingLeaseTerm1" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_OperatingLeaseWeightedAverageRemainingLeaseTerm1"/>
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    <link:label id="lab_us-gaap_DilutiveSecuritiesAbstract_92098f25-e962-4327-b376-76ef279b2f85_terseLabel_en-US" xlink:label="lab_us-gaap_DilutiveSecuritiesAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Effect of dilutive securities:</link:label>
    <link:label id="lab_us-gaap_DilutiveSecuritiesAbstract_label_en-US" xlink:label="lab_us-gaap_DilutiveSecuritiesAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Dilutive Securities, Effect on Basic Earnings Per Share [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DilutiveSecuritiesAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_DilutiveSecuritiesAbstract"/>
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    <link:label id="lab_root_UnearnedPremiumsGross_f3d96270-ead6-4c67-a6a0-567042d8d2bc_terseLabel_en-US" xlink:label="lab_root_UnearnedPremiumsGross" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Unearned premiums</link:label>
    <link:label id="lab_root_UnearnedPremiumsGross_label_en-US" xlink:label="lab_root_UnearnedPremiumsGross" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Unearned Premiums, Gross</link:label>
    <link:label id="lab_root_UnearnedPremiumsGross_documentation_en-US" xlink:label="lab_root_UnearnedPremiumsGross" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Unearned Premiums, Gross</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_root_UnearnedPremiumsGross" xlink:href="root-20251231.xsd#root_UnearnedPremiumsGross"/>
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    <link:label id="lab_dei_EntityPublicFloat_39eca379-6ffb-414b-9764-ee59cb81434e_terseLabel_en-US" xlink:label="lab_dei_EntityPublicFloat" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Entity Public Float</link:label>
    <link:label id="lab_dei_EntityPublicFloat_label_en-US" xlink:label="lab_dei_EntityPublicFloat" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Entity Public Float</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_EntityPublicFloat" xlink:href="https://xbrl.sec.gov/dei/2025/dei-2025.xsd#dei_EntityPublicFloat"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_EntityPublicFloat" xlink:to="lab_dei_EntityPublicFloat" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_InterestExpenseNonoperating_8bec343c-a77a-4532-a66b-aded38d32c4f_terseLabel_en-US" xlink:label="lab_us-gaap_InterestExpenseNonoperating" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Interest expense</link:label>
    <link:label id="lab_us-gaap_InterestExpenseNonoperating_c683ad38-1665-4aae-a37f-c1d1dfbfdc87_verboseLabel_en-US" xlink:label="lab_us-gaap_InterestExpenseNonoperating" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Interest expense</link:label>
    <link:label id="lab_us-gaap_InterestExpenseNonoperating_label_en-US" xlink:label="lab_us-gaap_InterestExpenseNonoperating" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Interest Expense, Nonoperating</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_InterestExpenseNonoperating" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_InterestExpenseNonoperating"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_InterestExpenseNonoperating" xlink:to="lab_us-gaap_InterestExpenseNonoperating" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_TradingArrAxis_terseLabel_en-US" xlink:label="lab_ecd_TradingArrAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Trading Arrangement:</link:label>
    <link:label id="lab_ecd_TradingArrAxis_label_en-US" xlink:label="lab_ecd_TradingArrAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Trading Arrangement [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_TradingArrAxis" xlink:href="https://xbrl.sec.gov/ecd/2025/ecd-2025.xsd#ecd_TradingArrAxis"/>
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    <link:label id="lab_ecd_TotalShareholderRtnAmt_terseLabel_en-US" xlink:label="lab_ecd_TotalShareholderRtnAmt" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Total Shareholder Return Amount</link:label>
    <link:label id="lab_ecd_TotalShareholderRtnAmt_label_en-US" xlink:label="lab_ecd_TotalShareholderRtnAmt" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Total Shareholder Return Amount</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_TotalShareholderRtnAmt" xlink:href="https://xbrl.sec.gov/ecd/2025/ecd-2025.xsd#ecd_TotalShareholderRtnAmt"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_TotalShareholderRtnAmt" xlink:to="lab_ecd_TotalShareholderRtnAmt" xlink:type="arc" order="1"/>
    <link:label id="lab_root_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseExchangeOfReinsuranceAgreements_20784ef1-337b-4313-9766-e188ce4fef93_terseLabel_en-US" xlink:label="lab_root_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseExchangeOfReinsuranceAgreements" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Incurred expense for commutations of certain reinsurance agreements</link:label>
    <link:label id="lab_root_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseExchangeOfReinsuranceAgreements_label_en-US" xlink:label="lab_root_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseExchangeOfReinsuranceAgreements" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Liability for Unpaid Claims and Claims Adjustment Expense, Exchange Of Reinsurance Agreements</link:label>
    <link:label id="lab_root_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseExchangeOfReinsuranceAgreements_documentation_en-US" xlink:label="lab_root_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseExchangeOfReinsuranceAgreements" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Liability for Unpaid Claims and Claims Adjustment Expense, Exchange Of Reinsurance Agreements</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_root_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseExchangeOfReinsuranceAgreements" xlink:href="root-20251231.xsd#root_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseExchangeOfReinsuranceAgreements"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_root_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseExchangeOfReinsuranceAgreements" xlink:to="lab_root_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseExchangeOfReinsuranceAgreements" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_SecurityExchangeName_510b8c08-44ac-45b1-b9c3-09bd081883a4_terseLabel_en-US" xlink:label="lab_dei_SecurityExchangeName" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2025/dei-2025.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_ReinsuranceRecoverablesAllowance_8043fdd1-791a-4b06-aba6-bd67f4e3ac91_verboseLabel_en-US" xlink:label="lab_us-gaap_ReinsuranceRecoverablesAllowance" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Allowance for credit loss</link:label>
    <link:label id="lab_us-gaap_ReinsuranceRecoverablesAllowance_3815386a-280d-4540-acfb-c8842a773e08_terseLabel_en-US" xlink:label="lab_us-gaap_ReinsuranceRecoverablesAllowance" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Provision for loss corridor</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" 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/2025/elts/us-gaap-2025.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_EffectiveIncomeTaxRateReconciliationCrossBorderTaxEffectPercentAbstract_019c7a8b-b366-71e5-9ad4-2d58673d1b68_terseLabel_en-US" xlink:label="lab_us-gaap_EffectiveIncomeTaxRateReconciliationCrossBorderTaxEffectPercentAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Effect of cross-border tax laws</link:label>
    <link:label id="lab_us-gaap_EffectiveIncomeTaxRateReconciliationCrossBorderTaxEffectPercentAbstract_label_en-US" xlink:label="lab_us-gaap_EffectiveIncomeTaxRateReconciliationCrossBorderTaxEffectPercentAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Effective Income Tax Rate Reconciliation, Cross-Border Tax Effect, Percent [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EffectiveIncomeTaxRateReconciliationCrossBorderTaxEffectPercentAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_EffectiveIncomeTaxRateReconciliationCrossBorderTaxEffectPercentAbstract"/>
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    <link:label id="lab_us-gaap_IncomeTaxReconciliationNondeductibleExpense_1ce05b0b-4a07-41fa-a4c0-7ccf9750cef0_terseLabel_en-US" xlink:label="lab_us-gaap_IncomeTaxReconciliationNondeductibleExpense" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Nondeductible compensation</link:label>
    <link:label id="lab_us-gaap_IncomeTaxReconciliationNondeductibleExpense_label_en-US" xlink:label="lab_us-gaap_IncomeTaxReconciliationNondeductibleExpense" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Effective Income Tax Rate Reconciliation, Nondeductible Expense, Amount</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncomeTaxReconciliationNondeductibleExpense" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_IncomeTaxReconciliationNondeductibleExpense"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IncomeTaxReconciliationNondeductibleExpense" xlink:to="lab_us-gaap_IncomeTaxReconciliationNondeductibleExpense" xlink:type="arc" order="1"/>
    <link:label id="lab_root_NonvestedSharesSubjectToRepurchaseMember_29054cc9-e782-4410-aee6-76647098cd69_terseLabel_en-US" xlink:label="lab_root_NonvestedSharesSubjectToRepurchaseMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Nonvested shares subject to repurchase</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" 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" xml:lang="en-US">Nonvested Shares Subject To Repurchase</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_root_NonvestedSharesSubjectToRepurchaseMember" xlink:href="root-20251231.xsd#root_NonvestedSharesSubjectToRepurchaseMember"/>
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    <link:label id="lab_root_EffectiveIncomeTaxRateReconciliationNondeductibleExpenseWarrantPercent_019c59d3-b0cc-744f-92a6-8d5232f3b5c5_terseLabel_en-US" xlink:label="lab_root_EffectiveIncomeTaxRateReconciliationNondeductibleExpenseWarrantPercent" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Nondeductible warrant expense</link:label>
    <link:label id="lab_root_EffectiveIncomeTaxRateReconciliationNondeductibleExpenseWarrantPercent_label_en-US" xlink:label="lab_root_EffectiveIncomeTaxRateReconciliationNondeductibleExpenseWarrantPercent" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Effective Income Tax Rate Reconciliation, Nondeductible Expense, Warrant, Percent</link:label>
    <link:label id="lab_root_EffectiveIncomeTaxRateReconciliationNondeductibleExpenseWarrantPercent_documentation_en-US" xlink:label="lab_root_EffectiveIncomeTaxRateReconciliationNondeductibleExpenseWarrantPercent" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Effective Income Tax Rate Reconciliation, Nondeductible Expense, Warrant, Percent</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_root_EffectiveIncomeTaxRateReconciliationNondeductibleExpenseWarrantPercent" xlink:href="root-20251231.xsd#root_EffectiveIncomeTaxRateReconciliationNondeductibleExpenseWarrantPercent"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_root_EffectiveIncomeTaxRateReconciliationNondeductibleExpenseWarrantPercent" xlink:to="lab_root_EffectiveIncomeTaxRateReconciliationNondeductibleExpenseWarrantPercent" xlink:type="arc" order="1"/>
    <link:label id="lab_root_StandardPoorsAAPlusAAAAMinusAMinusOnePlusRatingMember_855cd8f5-a0ac-43ea-b67c-ddd31622ab88_terseLabel_en-US" xlink:label="lab_root_StandardPoorsAAPlusAAAAMinusAMinusOnePlusRatingMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">AA+, AA, AA-, A-1+</link:label>
    <link:label id="lab_root_StandardPoorsAAPlusAAAAMinusAMinusOnePlusRatingMember_label_en-US" xlink:label="lab_root_StandardPoorsAAPlusAAAAMinusAMinusOnePlusRatingMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Standard &amp; Poor's, AA Plus, AA, AA Minus, A Minus One Plus Rating [Member]</link:label>
    <link:label id="lab_root_StandardPoorsAAPlusAAAAMinusAMinusOnePlusRatingMember_documentation_en-US" xlink:label="lab_root_StandardPoorsAAPlusAAAAMinusAMinusOnePlusRatingMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Standard &amp; Poor's, AA Plus, AA, AA Minus, A Minus One Plus Rating</link:label>
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    <link:label id="lab_us-gaap_CapitalizedComputerSoftwareNet_0ea06379-0734-43f7-9eec-4044f533b49a_totalLabel_en-US" xlink:label="lab_us-gaap_CapitalizedComputerSoftwareNet" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Internally developed software, net</link:label>
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    <link:label id="lab_us-gaap_ShortDurationInsuranceContractAccidentYear2023Member_01d922d1-a290-4f91-8591-af76b7a80ed8_terseLabel_en-US" xlink:label="lab_us-gaap_ShortDurationInsuranceContractAccidentYear2023Member" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">2023</link:label>
    <link:label id="lab_us-gaap_ShortDurationInsuranceContractAccidentYear2023Member_label_en-US" xlink:label="lab_us-gaap_ShortDurationInsuranceContractAccidentYear2023Member" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Short-Duration Insurance Contract, Accident Year 2023 [Member]</link:label>
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    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ShortDurationInsuranceContractAccidentYear2023Member" xlink:to="lab_us-gaap_ShortDurationInsuranceContractAccidentYear2023Member" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleExcludingAccruedInterestCurrent_f7938401-2072-4d49-a9fd-c7f335b19305_terseLabel_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleExcludingAccruedInterestCurrent" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Short-term investments (amortized cost: zero and $14.8 at December&#160;31, 2025 and December&#160;31, 2024, respectively)</link:label>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleExcludingAccruedInterestCurrent_label_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleExcludingAccruedInterestCurrent" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Available-for-Sale, Excluding Accrued Interest, Current</link:label>
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    <link:label id="lab_us-gaap_CededPremiumsEarned_95d7cd1d-bc78-4352-92ec-367bb54e94da_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_CededPremiumsEarned" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" 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" 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/2025/elts/us-gaap-2025.xsd#us-gaap_CededPremiumsEarned"/>
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    <link:label id="lab_root_OtherCertainRestrictedStockUnits3Member_a4cfbd67-4479-4c42-a03b-ab4194220960_terseLabel_en-US" xlink:label="lab_root_OtherCertainRestrictedStockUnits3Member" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Other Certain RSUs 3</link:label>
    <link:label id="lab_root_OtherCertainRestrictedStockUnits3Member_label_en-US" xlink:label="lab_root_OtherCertainRestrictedStockUnits3Member" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Other Certain Restricted Stock Units, 3 [Member]</link:label>
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    <link:loc xlink:type="locator" xlink:label="loc_root_OtherCertainRestrictedStockUnits3Member" xlink:href="root-20251231.xsd#root_OtherCertainRestrictedStockUnits3Member"/>
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    <link:label id="lab_us-gaap_OperatingExpensesAbstract_ecfa19f8-ae28-4127-a043-200d1e65fbc6_terseLabel_en-US" xlink:label="lab_us-gaap_OperatingExpensesAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Operating expenses:</link:label>
    <link:label id="lab_us-gaap_OperatingExpensesAbstract_3730f995-6bf3-42ab-89c5-0cabb420c615_verboseLabel_en-US" xlink:label="lab_us-gaap_OperatingExpensesAbstract" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Operating expenses:</link:label>
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    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OperatingExpensesAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_OperatingExpensesAbstract"/>
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    <link:label id="lab_us-gaap_ShortDurationInsuranceContractAccidentYear2022Member_258cd11b-f5bb-4e84-96bf-682be4f00ea1_terseLabel_en-US" xlink:label="lab_us-gaap_ShortDurationInsuranceContractAccidentYear2022Member" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">2022</link:label>
    <link:label id="lab_us-gaap_ShortDurationInsuranceContractAccidentYear2022Member_label_en-US" xlink:label="lab_us-gaap_ShortDurationInsuranceContractAccidentYear2022Member" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Short-Duration Insurance Contract, Accident Year 2022 [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShortDurationInsuranceContractAccidentYear2022Member" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_ShortDurationInsuranceContractAccidentYear2022Member"/>
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    <link:label id="lab_us-gaap_RedeemableConvertiblePreferredStockMember_d4dee386-1e15-4ab3-b405-f4408c182d3f_verboseLabel_en-US" xlink:label="lab_us-gaap_RedeemableConvertiblePreferredStockMember" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Redeemable convertible preferred stock</link:label>
    <link:label id="lab_us-gaap_RedeemableConvertiblePreferredStockMember_ec46223a-478c-42da-abd9-3a61e1b3b5da_terseLabel_en-US" xlink:label="lab_us-gaap_RedeemableConvertiblePreferredStockMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Redeemable convertible preferred stock (as converted to common stock)</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" 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/2025/elts/us-gaap-2025.xsd#us-gaap_RedeemableConvertiblePreferredStockMember"/>
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    <link:label id="lab_us-gaap_IncreaseDecreaseInTemporaryEquityRollForward_fd01275d-6021-4ecb-a805-98f88e5240a5_terseLabel_en-US" xlink:label="lab_us-gaap_IncreaseDecreaseInTemporaryEquityRollForward" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2025/elts/us-gaap-2025.xsd#us-gaap_IncreaseDecreaseInTemporaryEquityRollForward"/>
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    <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" xml:lang="en-US">Statement [Line Items]</link:label>
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    <link:label id="lab_us-gaap_ExtinguishmentOfDebtAmount_label_en-US" xlink:label="lab_us-gaap_ExtinguishmentOfDebtAmount" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Extinguishment of Debt, Amount</link:label>
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    <link:label id="lab_us-gaap_CashAndCashEquivalentsAtCarryingValue_0e859802-0720-4ca4-a92f-738b156f08e8_terseLabel_en-US" xlink:label="lab_us-gaap_CashAndCashEquivalentsAtCarryingValue" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" xml:lang="en-US">Cash and Cash Equivalent</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CashAndCashEquivalentsAtCarryingValue" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_CashAndCashEquivalentsAtCarryingValue"/>
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    <link:label id="lab_us-gaap_RestrictedStockValueSharesIssuedNetOfTaxWithholdings_c3c0a6ad-f61a-4465-bab3-506a0e2a447d_terseLabel_en-US" xlink:label="lab_us-gaap_RestrictedStockValueSharesIssuedNetOfTaxWithholdings" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Common stock&#8212;option exercises and restricted stock units vesting, net of shares withheld for employee taxes</link:label>
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    <link:label id="lab_us-gaap_ResearchMember_e7d45010-146f-4726-ba92-dea0268f99d5_terseLabel_en-US" xlink:label="lab_us-gaap_ResearchMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Research and development credits</link:label>
    <link:label id="lab_us-gaap_ResearchMember_label_en-US" xlink:label="lab_us-gaap_ResearchMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Research Tax Credit Carryforward [Member]</link:label>
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    <link:label id="lab_us-gaap_CommonStockMember_8520c69c-004c-46b1-b82b-2fef71e20fdd_verboseLabel_en-US" xlink:label="lab_us-gaap_CommonStockMember" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Class A and Class B Convertible Common Stock</link:label>
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    <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"/>
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    <link:label id="lab_root_LiabilityForClaimsAndClaimsAdjustmentExpenseGross_1dd4a47a-a855-435f-83dd-3c0c65a15bd4_terseLabel_en-US" xlink:label="lab_root_LiabilityForClaimsAndClaimsAdjustmentExpenseGross" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Loss and loss adjustment expense reserves</link:label>
    <link:label id="lab_root_LiabilityForClaimsAndClaimsAdjustmentExpenseGross_398e3130-ec50-4aee-976e-36d41b823701_periodStartLabel_en-US" xlink:label="lab_root_LiabilityForClaimsAndClaimsAdjustmentExpenseGross" xlink:role="http://www.xbrl.org/2003/role/periodStartLabel" xlink:type="resource" xml:lang="en-US">Gross loss and LAE reserves, January 1</link:label>
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    <link:loc xlink:type="locator" xlink:label="loc_srt_RangeMember" xlink:href="https://xbrl.fasb.org/srt/2025/elts/srt-2025.xsd#srt_RangeMember"/>
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    <link:label id="lab_us-gaap_IncomeLossFromEquityMethodInvestments_019c542e-e68e-7b32-bbbe-0a6198a9aff6_terseLabel_en-US" xlink:label="lab_us-gaap_IncomeLossFromEquityMethodInvestments" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Dividends from subsidiary</link:label>
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    <link:label id="lab_us-gaap_ClassOfWarrantOrRightOutstanding_750f2164-e6ce-4c92-ab3f-b7e2b8468bfe_terseLabel_en-US" xlink:label="lab_us-gaap_ClassOfWarrantOrRightOutstanding" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Warrants outstanding (in shares)</link:label>
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    <link:label id="lab_us-gaap_DeferredTaxAssetsOther_71d251f2-dd66-421f-8307-0dcab9e576ca_terseLabel_en-US" xlink:label="lab_us-gaap_DeferredTaxAssetsOther" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Other</link:label>
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    <link:label id="lab_us-gaap_GeneralAndAdministrativeExpenseMember_147348e9-a016-4632-8fa8-6f87081a036a_terseLabel_en-US" xlink:label="lab_us-gaap_GeneralAndAdministrativeExpenseMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">General and administrative</link:label>
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    <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" 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/2025/elts/us-gaap-2025.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_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsVestedInPeriodTotalFairValue_d5cf0301-efa4-434d-8db8-023bd0fe9c3d_terseLabel_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsVestedInPeriodTotalFairValue" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Total grant date fair value of awards vested</link:label>
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    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsVestedInPeriodTotalFairValue" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsVestedInPeriodTotalFairValue"/>
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    <link:label id="lab_root_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseAbstract_8d98995d-cb57-47bf-b9a1-255044cc461e_terseLabel_en-US" xlink:label="lab_root_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Loss and LAE reserves:</link:label>
    <link:label id="lab_root_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseAbstract_label_en-US" xlink:label="lab_root_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Liability For Unpaid Claims And Claims Adjustment Expense [Abstract]</link:label>
    <link:label id="lab_root_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseAbstract_documentation_en-US" xlink:label="lab_root_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseAbstract" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Liability For Unpaid Claims And Claims Adjustment Expense</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_root_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseAbstract" xlink:href="root-20251231.xsd#root_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_root_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseAbstract" xlink:to="lab_root_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_PayVsPerformanceDisclosureLineItems_label_en-US" xlink:label="lab_ecd_PayVsPerformanceDisclosureLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Pay vs Performance Disclosure [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_PayVsPerformanceDisclosureLineItems" xlink:href="https://xbrl.sec.gov/ecd/2025/ecd-2025.xsd#ecd_PayVsPerformanceDisclosureLineItems"/>
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    <link:label id="lab_us-gaap_ClassOfWarrantOrRightAxis_fe3cf87e-4906-472a-9ca2-190b5547481a_terseLabel_en-US" xlink:label="lab_us-gaap_ClassOfWarrantOrRightAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2025/elts/us-gaap-2025.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_OperatingLeaseLiability_e710d875-4fc9-4dca-a764-9cb1f0832485_verboseLabel_en-US" xlink:label="lab_us-gaap_OperatingLeaseLiability" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Operating lease liabilities</link:label>
    <link:label id="lab_us-gaap_OperatingLeaseLiability_760c62ee-8347-4ea5-9357-b716925a1d89_terseLabel_en-US" xlink:label="lab_us-gaap_OperatingLeaseLiability" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Total lease liabilities</link:label>
    <link:label id="lab_us-gaap_OperatingLeaseLiability_label_en-US" xlink:label="lab_us-gaap_OperatingLeaseLiability" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Operating Lease, Liability</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OperatingLeaseLiability" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_OperatingLeaseLiability"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_OperatingLeaseLiability" xlink:to="lab_us-gaap_OperatingLeaseLiability" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_IncreaseDecreaseInUnearnedPremiums_2e469844-0fc2-4368-923e-7a16be51c433_terseLabel_en-US" xlink:label="lab_us-gaap_IncreaseDecreaseInUnearnedPremiums" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2025/elts/us-gaap-2025.xsd#us-gaap_IncreaseDecreaseInUnearnedPremiums"/>
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    <link:label id="lab_us-gaap_EffectsOfReinsuranceTable_41ff90e7-8040-4b07-912a-6e751c47b52c_terseLabel_en-US" xlink:label="lab_us-gaap_EffectsOfReinsuranceTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2025/elts/us-gaap-2025.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_LiabilitiesAbstract_2e4cf6c1-069b-464a-aac4-9902b6957a74_terseLabel_en-US" xlink:label="lab_us-gaap_LiabilitiesAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Liabilities:</link:label>
    <link:label id="lab_us-gaap_LiabilitiesAbstract_d61d12a2-5439-4337-b2ee-9d43d0d34f62_verboseLabel_en-US" xlink:label="lab_us-gaap_LiabilitiesAbstract" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" 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" 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/2025/elts/us-gaap-2025.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_root_RootPropertyAndCasualtyMember_4a2d5d7c-ffa5-47f9-8a7b-9d2a13465039_terseLabel_en-US" xlink:label="lab_root_RootPropertyAndCasualtyMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Root Property &amp; Casualty</link:label>
    <link:label id="lab_root_RootPropertyAndCasualtyMember_label_en-US" xlink:label="lab_root_RootPropertyAndCasualtyMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Root Property And Casualty [Member]</link:label>
    <link:label id="lab_root_RootPropertyAndCasualtyMember_documentation_en-US" xlink:label="lab_root_RootPropertyAndCasualtyMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Root Property And Casualty</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_root_RootPropertyAndCasualtyMember" xlink:href="root-20251231.xsd#root_RootPropertyAndCasualtyMember"/>
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    <link:label id="lab_us-gaap_SummaryOfValuationAllowanceTextBlock_3c580c7e-cb09-4853-bc95-499a0021c735_terseLabel_en-US" xlink:label="lab_us-gaap_SummaryOfValuationAllowanceTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Schedule of Valuation Allowance</link:label>
    <link:label id="lab_us-gaap_SummaryOfValuationAllowanceTextBlock_label_en-US" xlink:label="lab_us-gaap_SummaryOfValuationAllowanceTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Summary of Valuation Allowance [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SummaryOfValuationAllowanceTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_SummaryOfValuationAllowanceTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_SummaryOfValuationAllowanceTextBlock" xlink:to="lab_us-gaap_SummaryOfValuationAllowanceTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ShareBasedCompensationSharesAuthorizedUnderStockOptionPlansExercisePriceRangeNumberOfExercisableOptions_24501a7f-c17a-43c5-969e-8a4e57707c53_terseLabel_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationSharesAuthorizedUnderStockOptionPlansExercisePriceRangeNumberOfExercisableOptions" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Options exercisable, number of shares (in shares)</link:label>
    <link:label id="lab_us-gaap_ShareBasedCompensationSharesAuthorizedUnderStockOptionPlansExercisePriceRangeNumberOfExercisableOptions_label_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationSharesAuthorizedUnderStockOptionPlansExercisePriceRangeNumberOfExercisableOptions" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Share-Based Payment Arrangement, Option, Exercise Price Range, Shares Exercisable</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShareBasedCompensationSharesAuthorizedUnderStockOptionPlansExercisePriceRangeNumberOfExercisableOptions" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_ShareBasedCompensationSharesAuthorizedUnderStockOptionPlansExercisePriceRangeNumberOfExercisableOptions"/>
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    <link:label id="lab_us-gaap_ShareBasedCompensationSharesAuthorizedUnderStockOptionPlansExercisePriceRangeUpperRangeLimit_f1363f95-9311-4869-9ced-32ac13fda95e_terseLabel_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationSharesAuthorizedUnderStockOptionPlansExercisePriceRangeUpperRangeLimit" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Exercise price range, max (in dollars per share)</link:label>
    <link:label id="lab_us-gaap_ShareBasedCompensationSharesAuthorizedUnderStockOptionPlansExercisePriceRangeUpperRangeLimit_label_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationSharesAuthorizedUnderStockOptionPlansExercisePriceRangeUpperRangeLimit" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Share-Based Payment Arrangement, Option, Exercise Price Range, Upper Range Limit</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShareBasedCompensationSharesAuthorizedUnderStockOptionPlansExercisePriceRangeUpperRangeLimit" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_ShareBasedCompensationSharesAuthorizedUnderStockOptionPlansExercisePriceRangeUpperRangeLimit"/>
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    <link:label id="lab_us-gaap_StatementOfCashFlowsAbstract_a704f3ec-3b99-40a1-8d6a-118f4f3540d0_terseLabel_en-US" xlink:label="lab_us-gaap_StatementOfCashFlowsAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Statement of Cash Flows [Abstract]</link:label>
    <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" 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/2025/elts/us-gaap-2025.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_ecd_CoSelectedMeasureAmt_terseLabel_en-US" xlink:label="lab_ecd_CoSelectedMeasureAmt" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Company Selected Measure Amount</link:label>
    <link:label id="lab_ecd_CoSelectedMeasureAmt_label_en-US" xlink:label="lab_ecd_CoSelectedMeasureAmt" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Company Selected Measure Amount</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_CoSelectedMeasureAmt" xlink:href="https://xbrl.sec.gov/ecd/2025/ecd-2025.xsd#ecd_CoSelectedMeasureAmt"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_CoSelectedMeasureAmt" xlink:to="lab_ecd_CoSelectedMeasureAmt" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LesseeOperatingLeaseLiabilityPaymentsDueYearThree_b61a6427-fffc-413e-8c4f-7062a2d0e2f3_terseLabel_en-US" xlink:label="lab_us-gaap_LesseeOperatingLeaseLiabilityPaymentsDueYearThree" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">2028</link:label>
    <link:label id="lab_us-gaap_LesseeOperatingLeaseLiabilityPaymentsDueYearThree_label_en-US" xlink:label="lab_us-gaap_LesseeOperatingLeaseLiabilityPaymentsDueYearThree" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Lessee, Operating Lease, Liability, to be Paid, Year Three</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LesseeOperatingLeaseLiabilityPaymentsDueYearThree" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_LesseeOperatingLeaseLiabilityPaymentsDueYearThree"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LesseeOperatingLeaseLiabilityPaymentsDueYearThree" xlink:to="lab_us-gaap_LesseeOperatingLeaseLiabilityPaymentsDueYearThree" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ComprehensiveIncomeNetOfTax_2818bc71-67ab-4f92-bb15-a7ea9d07570a_totalLabel_en-US" xlink:label="lab_us-gaap_ComprehensiveIncomeNetOfTax" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Comprehensive income (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" 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/2025/elts/us-gaap-2025.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_ecd_MeasureName_terseLabel_en-US" xlink:label="lab_ecd_MeasureName" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Name</link:label>
    <link:label id="lab_ecd_MeasureName_label_en-US" xlink:label="lab_ecd_MeasureName" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Measure Name</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_MeasureName" xlink:href="https://xbrl.sec.gov/ecd/2025/ecd-2025.xsd#ecd_MeasureName"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_MeasureName" xlink:to="lab_ecd_MeasureName" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesWithinOneYearFairValue_c72d112d-508f-413e-b97d-a7018d052a72_verboseLabel_en-US" xlink:label="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesWithinOneYearFairValue" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Due in one year or less</link:label>
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    <link:label id="lab_us-gaap_SecuredDebtMember_6a947324-07c0-432a-8c72-085fdcbc4839_terseLabel_en-US" xlink:label="lab_us-gaap_SecuredDebtMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2025/elts/us-gaap-2025.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_ProceedsFromMaturitiesPrepaymentsAndCallsOfAvailableForSaleSecurities_a2a93e49-04f2-490f-8cc2-897121506e24_terseLabel_en-US" xlink:label="lab_us-gaap_ProceedsFromMaturitiesPrepaymentsAndCallsOfAvailableForSaleSecurities" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Proceeds from maturities, call and pay downs of investments</link:label>
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    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ProceedsFromMaturitiesPrepaymentsAndCallsOfAvailableForSaleSecurities" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_ProceedsFromMaturitiesPrepaymentsAndCallsOfAvailableForSaleSecurities"/>
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    <link:label id="lab_us-gaap_AssumedPremiumsWritten_00013552-1ba2-4e0a-af43-94e0eea56c15_terseLabel_en-US" xlink:label="lab_us-gaap_AssumedPremiumsWritten" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" xml:lang="en-US">Assumed Premiums Written</link:label>
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    <link:label id="lab_root_TaxCreditCarryforwardSubjectToExpiration_label_en-US" xlink:label="lab_root_TaxCreditCarryforwardSubjectToExpiration" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Tax Credit Carryforward, Subject To Expiration</link:label>
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    <link:label id="lab_srt_ValuationAndQualifyingAccountsDisclosureTable_f061e226-9d87-4228-b1e5-1e58aaa7fadc_terseLabel_en-US" xlink:label="lab_srt_ValuationAndQualifyingAccountsDisclosureTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">SEC Schedule, 12-09, Valuation and Qualifying Accounts Disclosure [Table]</link:label>
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    <link:label id="lab_us-gaap_LongTermDebt_f9032bf4-8cbd-49d7-844f-5f9bc7e578d5_verboseLabel_en-US" xlink:label="lab_us-gaap_LongTermDebt" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Long-term debt</link:label>
    <link:label id="lab_us-gaap_LongTermDebt_6de55b27-a629-430a-b8c3-e11b4e676303_totalLabel_en-US" xlink:label="lab_us-gaap_LongTermDebt" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Total</link:label>
    <link:label id="lab_us-gaap_LongTermDebt_90f342c2-3c50-4abd-89ea-6756edf9c73e_terseLabel_en-US" xlink:label="lab_us-gaap_LongTermDebt" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Long-term debt</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" xml:lang="en-US">Long-Term Debt</link:label>
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    <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_dei_LegalEntityAxis_cdeb3f20-b1fa-4331-b19e-8af7d389ac0d_terseLabel_en-US" xlink:label="lab_dei_LegalEntityAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Legal Entity [Axis]</link:label>
    <link:label id="lab_dei_LegalEntityAxis_label_en-US" xlink:label="lab_dei_LegalEntityAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Legal Entity [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_LegalEntityAxis" xlink:href="https://xbrl.sec.gov/dei/2025/dei-2025.xsd#dei_LegalEntityAxis"/>
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    <link:label id="lab_root_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsGross_38efd413-6035-4618-bf90-61e61a91ccb5_terseLabel_en-US" xlink:label="lab_root_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsGross" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" xml:lang="en-US">Liability For Unpaid Claims And Claims Adjustment Expense, Incurred Claims, Gross</link:label>
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    <link:label id="lab_us-gaap_Assets_69e25de2-2ca3-4e7b-8cc3-0e3a2c660691_totalLabel_en-US" xlink:label="lab_us-gaap_Assets" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" 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" 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/2025/elts/us-gaap-2025.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_srt_ScheduleOfCondensedCashFlowStatementTableTextBlock_37199f8e-b8da-4df4-a270-6947e0ce7b2f_terseLabel_en-US" xlink:label="lab_srt_ScheduleOfCondensedCashFlowStatementTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Schedule of Condensed Cash Flow Statement</link:label>
    <link:label id="lab_srt_ScheduleOfCondensedCashFlowStatementTableTextBlock_label_en-US" xlink:label="lab_srt_ScheduleOfCondensedCashFlowStatementTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Condensed Cash Flow Statement [Table Text Block]</link:label>
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    <link:label id="lab_root_RootInsuranceAgencyLLCMember_019c7149-b00f-7aa3-8463-b09e91533d49_terseLabel_en-US" xlink:label="lab_root_RootInsuranceAgencyLLCMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Root Insurance Agency, LLC</link:label>
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    <link:label id="lab_us-gaap_ScheduleOfNonvestedRestrictedStockUnitsActivityTableTextBlock_c1290413-9168-4811-8511-6c6da83d918e_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfNonvestedRestrictedStockUnitsActivityTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Schedule of RSU, PRSU and MRSU Activity</link:label>
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    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsVestedInPeriodWeightedAverageGrantDateFairValue_9d727efb-1051-4682-a249-52d0cae8d110_terseLabel_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsVestedInPeriodWeightedAverageGrantDateFairValue" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Vested (in dollars per shares)</link:label>
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    <link:label id="lab_srt_SegmentGeographicalDomain_f83c0b12-6e43-4caf-9d4a-0e7e825b977b_terseLabel_en-US" xlink:label="lab_srt_SegmentGeographicalDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Geographical [Domain]</link:label>
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    <link:label id="lab_us-gaap_IncomeTaxPolicyTextBlock_a8084e90-7214-4d95-8fbe-d9fce2ae18bc_terseLabel_en-US" xlink:label="lab_us-gaap_IncomeTaxPolicyTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Income Taxes</link:label>
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    <link:loc xlink:type="locator" xlink:label="loc_root_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseLossesNet" xlink:href="root-20251231.xsd#root_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseLossesNet"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_root_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseLossesNet" xlink:to="lab_root_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseLossesNet" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_NetCashProvidedByUsedInOperatingActivitiesAbstract_5147028e-1b2f-41ad-b934-ba92d5b04786_terseLabel_en-US" xlink:label="lab_us-gaap_NetCashProvidedByUsedInOperatingActivitiesAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Cash flows from operating activities:</link:label>
    <link:label id="lab_us-gaap_NetCashProvidedByUsedInOperatingActivitiesAbstract_0fc028bd-fbd5-4990-b3f1-c52964e79f97_verboseLabel_en-US" xlink:label="lab_us-gaap_NetCashProvidedByUsedInOperatingActivitiesAbstract" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" 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" xml:lang="en-US">Cash Provided by (Used in) Operating Activity, Including Discontinued Operation [Abstract]</link:label>
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    <link:label id="lab_us-gaap_ConcentrationRiskByTypeAxis_c6dc4a93-25fd-45f4-a252-62b483ec28a6_terseLabel_en-US" xlink:label="lab_us-gaap_ConcentrationRiskByTypeAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" xml:lang="en-US">Concentration Risk Type [Axis]</link:label>
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    <link:label id="lab_root_RootIncMember_cc1fa98a-c3a6-4ef8-8320-aef5402266a1_terseLabel_en-US" xlink:label="lab_root_RootIncMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Root, Inc</link:label>
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    <link:label id="lab_us-gaap_ShortdurationInsuranceContractsClaimsDevelopmentTable_af122f83-cee1-41cc-b6fd-b2385995d38a_terseLabel_en-US" xlink:label="lab_us-gaap_ShortdurationInsuranceContractsClaimsDevelopmentTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Short-duration Insurance Contracts, Claims Development [Table]</link:label>
    <link:label id="lab_us-gaap_ShortdurationInsuranceContractsClaimsDevelopmentTable_label_en-US" xlink:label="lab_us-gaap_ShortdurationInsuranceContractsClaimsDevelopmentTable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Short-Duration Insurance Contracts, Claims Development [Table]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShortdurationInsuranceContractsClaimsDevelopmentTable" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_ShortdurationInsuranceContractsClaimsDevelopmentTable"/>
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    <link:label id="lab_us-gaap_AssetsFairValueDisclosureAbstract_0a219d91-c763-4ae6-ab2d-27bcc36e8923_terseLabel_en-US" xlink:label="lab_us-gaap_AssetsFairValueDisclosureAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2025/elts/us-gaap-2025.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_RestructuringCosts_0508f352-9bdb-4917-99d5-a0209048440e_terseLabel_en-US" xlink:label="lab_us-gaap_RestructuringCosts" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" xml:lang="en-US">Restructuring Costs</link:label>
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    <link:label id="lab_us-gaap_WarrantMember_b39cea72-77a2-43ef-b725-8f05261aece8_terseLabel_en-US" xlink:label="lab_us-gaap_WarrantMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Warrant</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" 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/2025/elts/us-gaap-2025.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_us-gaap_OtherInvestments_d8e295c0-39ac-458b-b704-ae9ba390a0b2_terseLabel_en-US" xlink:label="lab_us-gaap_OtherInvestments" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Other investments</link:label>
    <link:label id="lab_us-gaap_OtherInvestments_94aab78d-220f-4bbe-be4e-e3c4c48c3fcf_verboseLabel_en-US" xlink:label="lab_us-gaap_OtherInvestments" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" 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" 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/2025/elts/us-gaap-2025.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_dei_EntityCommonStockSharesOutstanding_e1f27e70-ed4d-4769-b943-63301eaa83f1_terseLabel_en-US" xlink:label="lab_dei_EntityCommonStockSharesOutstanding" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2025/dei-2025.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_ShortdurationInsuranceContractsLiabilityForUnpaidClaimsAndAllocatedClaimAdjustmentExpenseNet_9d520da2-470c-4c63-96b8-c938f50ff585_totalLabel_en-US" xlink:label="lab_us-gaap_ShortdurationInsuranceContractsLiabilityForUnpaidClaimsAndAllocatedClaimAdjustmentExpenseNet" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Loss and ALAE reserves&#8212;net of reinsurance</link:label>
    <link:label id="lab_us-gaap_ShortdurationInsuranceContractsLiabilityForUnpaidClaimsAndAllocatedClaimAdjustmentExpenseNet_label_en-US" xlink:label="lab_us-gaap_ShortdurationInsuranceContractsLiabilityForUnpaidClaimsAndAllocatedClaimAdjustmentExpenseNet" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Short-Duration Insurance Contracts, Liability for Unpaid Claims and Allocated Claim Adjustment Expense, Net</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShortdurationInsuranceContractsLiabilityForUnpaidClaimsAndAllocatedClaimAdjustmentExpenseNet" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_ShortdurationInsuranceContractsLiabilityForUnpaidClaimsAndAllocatedClaimAdjustmentExpenseNet"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ShortdurationInsuranceContractsLiabilityForUnpaidClaimsAndAllocatedClaimAdjustmentExpenseNet" xlink:to="lab_us-gaap_ShortdurationInsuranceContractsLiabilityForUnpaidClaimsAndAllocatedClaimAdjustmentExpenseNet" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ScheduleOfAvailableForSaleSecuritiesLineItems_a4e33236-ae58-4ee3-8642-531881d5f5b8_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfAvailableForSaleSecuritiesLineItems" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2025/elts/us-gaap-2025.xsd#us-gaap_ScheduleOfAvailableForSaleSecuritiesLineItems"/>
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    <link:label id="lab_us-gaap_PrepaidReinsurancePremiums_2adb1887-e4ef-4037-a9dc-a9cedd7e7b65_terseLabel_en-US" xlink:label="lab_us-gaap_PrepaidReinsurancePremiums" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Prepaid reinsurance premiums</link:label>
    <link:label id="lab_us-gaap_PrepaidReinsurancePremiums_1d636047-166e-42a3-84b3-239ada1c7876_negatedLabel_en-US" xlink:label="lab_us-gaap_PrepaidReinsurancePremiums" xlink:role="http://www.xbrl.org/2009/role/negatedLabel" xlink:type="resource" xml:lang="en-US">Ceded</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" 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/2025/elts/us-gaap-2025.xsd#us-gaap_PrepaidReinsurancePremiums"/>
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    <link:label id="lab_us-gaap_FairValueInputsLevel2Member_4e376ced-1d4a-4701-8864-abc15cb0fd41_terseLabel_en-US" xlink:label="lab_us-gaap_FairValueInputsLevel2Member" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" xml:lang="en-US">Fair Value, Inputs, Level 2 [Member]</link:label>
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    <link:label id="lab_us-gaap_IncomeTaxReconciliationStateAndLocalIncomeTaxes_019b6df9-21e7-749b-9d10-aacd5b2e869c_terseLabel_en-US" xlink:label="lab_us-gaap_IncomeTaxReconciliationStateAndLocalIncomeTaxes" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">State and local income tax expense, net of federal income tax effect</link:label>
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    <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" 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/2025/elts/us-gaap-2025.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_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPosition12MonthsOrLonger_96d43bef-5787-48eb-8099-61a800da34a5_terseLabel_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPosition12MonthsOrLonger" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">12 Months or More</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" 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/2025/elts/us-gaap-2025.xsd#us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPosition12MonthsOrLonger"/>
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    <link:label id="lab_us-gaap_PremiumsWrittenNetConsolidatedAbstract_1231ec0d-70b9-407c-bf5e-bcf126c118ec_terseLabel_en-US" xlink:label="lab_us-gaap_PremiumsWrittenNetConsolidatedAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2025/elts/us-gaap-2025.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_SaleOfStockNameOfTransactionDomain_eeceeb63-3d6b-4807-a90e-345a6a6161c2_terseLabel_en-US" xlink:label="lab_us-gaap_SaleOfStockNameOfTransactionDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Sale of Stock [Domain]</link:label>
    <link:label id="lab_us-gaap_SaleOfStockNameOfTransactionDomain_label_en-US" xlink:label="lab_us-gaap_SaleOfStockNameOfTransactionDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Sale of Stock [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SaleOfStockNameOfTransactionDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_SaleOfStockNameOfTransactionDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_SaleOfStockNameOfTransactionDomain" xlink:to="lab_us-gaap_SaleOfStockNameOfTransactionDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_NetInvestmentIncome_b9ec3e2a-b1fd-4651-a461-dad0e2c0e633_terseLabel_en-US" xlink:label="lab_us-gaap_NetInvestmentIncome" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Net investment income</link:label>
    <link:label id="lab_us-gaap_NetInvestmentIncome_0086eb6c-ae6c-41bf-9e4d-2b421dad4e54_totalLabel_en-US" xlink:label="lab_us-gaap_NetInvestmentIncome" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Net investment income</link:label>
    <link:label id="lab_us-gaap_NetInvestmentIncome_76a31f6d-4389-4f02-8b9a-1136d40ac99e_verboseLabel_en-US" xlink:label="lab_us-gaap_NetInvestmentIncome" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" 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" 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/2025/elts/us-gaap-2025.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_ecd_RestatementDoesNotRequireRecoveryTextBlock_terseLabel_en-US" xlink:label="lab_ecd_RestatementDoesNotRequireRecoveryTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Restatement does not require Recovery</link:label>
    <link:label id="lab_ecd_RestatementDoesNotRequireRecoveryTextBlock_label_en-US" xlink:label="lab_ecd_RestatementDoesNotRequireRecoveryTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Restatement Does Not Require Recovery [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_RestatementDoesNotRequireRecoveryTextBlock" xlink:href="https://xbrl.sec.gov/ecd/2025/ecd-2025.xsd#ecd_RestatementDoesNotRequireRecoveryTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_RestatementDoesNotRequireRecoveryTextBlock" xlink:to="lab_ecd_RestatementDoesNotRequireRecoveryTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_OrganizationConsolidationAndPresentationOfFinancialStatementsAbstract_1c789265-5587-4500-ab7b-3588d52d7b4e_terseLabel_en-US" xlink:label="lab_us-gaap_OrganizationConsolidationAndPresentationOfFinancialStatementsAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Organization, Consolidation and Presentation of Financial Statements [Abstract]</link:label>
    <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" 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/2025/elts/us-gaap-2025.xsd#us-gaap_OrganizationConsolidationAndPresentationOfFinancialStatementsAbstract"/>
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    <link:label id="lab_us-gaap_FairValueLiabilitiesMeasuredOnRecurringAndNonrecurringBasisTableTextBlock_ece09e1a-e342-4e85-87bf-59fe89848221_terseLabel_en-US" xlink:label="lab_us-gaap_FairValueLiabilitiesMeasuredOnRecurringAndNonrecurringBasisTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2025/elts/us-gaap-2025.xsd#us-gaap_FairValueLiabilitiesMeasuredOnRecurringAndNonrecurringBasisTableTextBlock"/>
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    <link:label id="lab_us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationYearFive_f255c6c1-af86-4894-a121-e39b30c92a77_terseLabel_en-US" xlink:label="lab_us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationYearFive" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Incremental paid, year 5</link:label>
    <link:label id="lab_us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationYearFive_label_en-US" xlink:label="lab_us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationYearFive" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Short-Duration Insurance Contracts, Historical Claims Duration, Year Five</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationYearFive" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationYearFive"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationYearFive" xlink:to="lab_us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationYearFive" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_CityAreaCode_a623f0ce-3195-48d4-a9b7-23b7ded4bd23_terseLabel_en-US" xlink:label="lab_dei_CityAreaCode" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2025/dei-2025.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_ecd_AwardTmgHowMnpiCnsdrdTextBlock_terseLabel_en-US" xlink:label="lab_ecd_AwardTmgHowMnpiCnsdrdTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Award Timing, How MNPI Considered</link:label>
    <link:label id="lab_ecd_AwardTmgHowMnpiCnsdrdTextBlock_label_en-US" xlink:label="lab_ecd_AwardTmgHowMnpiCnsdrdTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Award Timing, How MNPI Considered [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_AwardTmgHowMnpiCnsdrdTextBlock" xlink:href="https://xbrl.sec.gov/ecd/2025/ecd-2025.xsd#ecd_AwardTmgHowMnpiCnsdrdTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_AwardTmgHowMnpiCnsdrdTextBlock" xlink:to="lab_ecd_AwardTmgHowMnpiCnsdrdTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_root_LesseeOperatingLeaseLiabilityToBePaidAfterYearFour_77865cb0-0e46-42ab-bc55-1fb86c7712f2_terseLabel_en-US" xlink:label="lab_root_LesseeOperatingLeaseLiabilityToBePaidAfterYearFour" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">2030 and thereafter</link:label>
    <link:label id="lab_root_LesseeOperatingLeaseLiabilityToBePaidAfterYearFour_label_en-US" xlink:label="lab_root_LesseeOperatingLeaseLiabilityToBePaidAfterYearFour" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Lessee, Operating Lease, Liability, to be Paid, after Year Four</link:label>
    <link:label id="lab_root_LesseeOperatingLeaseLiabilityToBePaidAfterYearFour_documentation_en-US" xlink:label="lab_root_LesseeOperatingLeaseLiabilityToBePaidAfterYearFour" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Lessee, Operating Lease, Liability, to be Paid, after Year Four</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_root_LesseeOperatingLeaseLiabilityToBePaidAfterYearFour" xlink:href="root-20251231.xsd#root_LesseeOperatingLeaseLiabilityToBePaidAfterYearFour"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_root_LesseeOperatingLeaseLiabilityToBePaidAfterYearFour" xlink:to="lab_root_LesseeOperatingLeaseLiabilityToBePaidAfterYearFour" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_InvestmentTextBlock_16c038fa-9a8e-48a4-b287-f21df90f39d6_terseLabel_en-US" xlink:label="lab_us-gaap_InvestmentTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2025/elts/us-gaap-2025.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_root_ShareBasedCompensationArrangementByShareBasedPaymentAwardBaseNumberOfOptionsIssuable_5cacf32c-8635-494d-a0e8-16777529185d_terseLabel_en-US" xlink:label="lab_root_ShareBasedCompensationArrangementByShareBasedPaymentAwardBaseNumberOfOptionsIssuable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Maximum shares allowed to be issued (in shares)</link:label>
    <link:label id="lab_root_ShareBasedCompensationArrangementByShareBasedPaymentAwardBaseNumberOfOptionsIssuable_label_en-US" xlink:label="lab_root_ShareBasedCompensationArrangementByShareBasedPaymentAwardBaseNumberOfOptionsIssuable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Share-based Compensation Arrangement by Share-based Payment Award, Base Number Of Options Issuable</link:label>
    <link:label id="lab_root_ShareBasedCompensationArrangementByShareBasedPaymentAwardBaseNumberOfOptionsIssuable_documentation_en-US" xlink:label="lab_root_ShareBasedCompensationArrangementByShareBasedPaymentAwardBaseNumberOfOptionsIssuable" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Share-based Compensation Arrangement by Share-based Payment Award, Base Number Of Options Issuable</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_root_ShareBasedCompensationArrangementByShareBasedPaymentAwardBaseNumberOfOptionsIssuable" xlink:href="root-20251231.xsd#root_ShareBasedCompensationArrangementByShareBasedPaymentAwardBaseNumberOfOptionsIssuable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_root_ShareBasedCompensationArrangementByShareBasedPaymentAwardBaseNumberOfOptionsIssuable" xlink:to="lab_root_ShareBasedCompensationArrangementByShareBasedPaymentAwardBaseNumberOfOptionsIssuable" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ClassOfWarrantOrRightLineItems_0aae43b7-d343-4b85-ae51-d06ee0201617_terseLabel_en-US" xlink:label="lab_us-gaap_ClassOfWarrantOrRightLineItems" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Class of Warrant or Right [Line Items]</link:label>
    <link:label id="lab_us-gaap_ClassOfWarrantOrRightLineItems_label_en-US" xlink:label="lab_us-gaap_ClassOfWarrantOrRightLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Class of Warrant or Right [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ClassOfWarrantOrRightLineItems" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_ClassOfWarrantOrRightLineItems"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ClassOfWarrantOrRightLineItems" xlink:to="lab_us-gaap_ClassOfWarrantOrRightLineItems" xlink:type="arc" order="1"/>
    <link:label id="lab_root_AmendedTermLoanCMember_e4754e43-8d7a-4b6f-868c-97560eabfc16_terseLabel_en-US" xlink:label="lab_root_AmendedTermLoanCMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Amended Term Loan C</link:label>
    <link:label id="lab_root_AmendedTermLoanCMember_label_en-US" xlink:label="lab_root_AmendedTermLoanCMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Amended Term Loan C [Member]</link:label>
    <link:label id="lab_root_AmendedTermLoanCMember_documentation_en-US" xlink:label="lab_root_AmendedTermLoanCMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Amended Term Loan C</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_root_AmendedTermLoanCMember" xlink:href="root-20251231.xsd#root_AmendedTermLoanCMember"/>
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    <link:label id="lab_root_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsAssumed_7ed240ea-c744-4b9a-af16-580112136fe4_terseLabel_en-US" xlink:label="lab_root_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsAssumed" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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" 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-20251231.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"/>
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    <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" xml:lang="en-US">General and Administrative Expense</link:label>
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    <link:label id="lab_us-gaap_OperatingLeaseLiabilityStatementOfFinancialPositionExtensibleList_427434fe-f3df-4f3a-854b-2db0e05b06b8_terseLabel_en-US" xlink:label="lab_us-gaap_OperatingLeaseLiabilityStatementOfFinancialPositionExtensibleList" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Operating lease, liability, statement of financial position [Extensible Enumeration]</link:label>
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    <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" xml:lang="en-US">Other Liabilities</link:label>
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    <link:label id="lab_us-gaap_LeaseCostTableTextBlock_label_en-US" xlink:label="lab_us-gaap_LeaseCostTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Lease, Cost [Table Text Block]</link:label>
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    <link:label id="lab_us-gaap_DeferredTaxAssetInterestCarryforward_964e09ef-6bf1-4886-bdc1-fa2e2837bb34_terseLabel_en-US" xlink:label="lab_us-gaap_DeferredTaxAssetInterestCarryforward" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Disallowed interest carryforward</link:label>
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    <link:label id="lab_dei_AuditorName_6136210e-0478-4d81-9866-680d7146f7ed_terseLabel_en-US" xlink:label="lab_dei_AuditorName" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Auditor Name</link:label>
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    <link:label id="lab_us-gaap_EffectiveIncomeTaxRateReconciliationShareBasedCompensationExcessTaxBenefitAmount_019c59d3-b0cc-7525-ab33-eb9656728184_terseLabel_en-US" xlink:label="lab_us-gaap_EffectiveIncomeTaxRateReconciliationShareBasedCompensationExcessTaxBenefitAmount" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Nondeductible compensation</link:label>
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    <link:label id="lab_us-gaap_FairValueMeasurementPolicyPolicyTextBlock_label_en-US" xlink:label="lab_us-gaap_FairValueMeasurementPolicyPolicyTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Fair Value Measurement, Policy [Policy Text Block]</link:label>
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    <link:label id="lab_us-gaap_IncomeTaxExpenseBenefitContinuingOperationsIncomeTaxReconciliationAbstract_label_en-US" xlink:label="lab_us-gaap_IncomeTaxExpenseBenefitContinuingOperationsIncomeTaxReconciliationAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Income Tax Expense (Benefit), Effective Income Tax Rate Reconciliation, Amount [Abstract]</link:label>
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    <link:label id="lab_root_RegulatoryAssetRequirementSpecialDepositsHeldInTrust_019c7a5d-ad9a-7afc-98b7-1c15a9892f3a_terseLabel_en-US" xlink:label="lab_root_RegulatoryAssetRequirementSpecialDepositsHeldInTrust" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Balances held in the trust</link:label>
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    <link:label id="lab_root_RegulatoryAssetRequirementSpecialDepositsHeldInTrust_documentation_en-US" xlink:label="lab_root_RegulatoryAssetRequirementSpecialDepositsHeldInTrust" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Regulatory Asset Requirement, Special Deposits, Held In Trust</link:label>
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    <link:label id="lab_root_NetIncomeLossAttributableToParentBeforeIncomeLossFromSubsidiariesAfterTax_8e112d93-48f8-4047-a994-35c491549aed_totalLabel_en-US" xlink:label="lab_root_NetIncomeLossAttributableToParentBeforeIncomeLossFromSubsidiariesAfterTax" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Net loss before equity net income (loss) of subsidiaries</link:label>
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    <link:label id="lab_us-gaap_RestrictedCash_c0e75363-7914-455d-b937-578d3f70f0d2_terseLabel_en-US" xlink:label="lab_us-gaap_RestrictedCash" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Restricted cash and cash equivalents</link:label>
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    <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" xml:lang="en-US">Restricted Cash</link:label>
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    <link:label id="lab_us-gaap_VestingAxis_7b7fe3a5-8674-4b15-adbe-942843392656_terseLabel_en-US" xlink:label="lab_us-gaap_VestingAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2025/elts/us-gaap-2025.xsd#us-gaap_VestingAxis"/>
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    <link:label id="lab_root_RootReinsuranceCompanyLtdMember_20be4768-194e-4c6f-b747-ff60684699f2_terseLabel_en-US" xlink:label="lab_root_RootReinsuranceCompanyLtdMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Root Reinsurance Company, Ltd.</link:label>
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    <link:label id="lab_root_A2020EquityIncentivePlanMember_2b34c449-443c-4d47-826c-3d897b974782_terseLabel_en-US" xlink:label="lab_root_A2020EquityIncentivePlanMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">2020 Plan</link:label>
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    <link:label id="lab_us-gaap_InvestmentsAbstract_a3fd6581-a5fe-4ae5-8b14-5c52ae765d6d_terseLabel_en-US" xlink:label="lab_us-gaap_InvestmentsAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" xml:lang="en-US">Investments [Abstract]</link:label>
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    <link:label id="lab_us-gaap_InvestmentsInAffiliatesSubsidiariesAssociatesAndJointVentures_949a72fa-b707-434a-9bb1-af1083765c14_terseLabel_en-US" xlink:label="lab_us-gaap_InvestmentsInAffiliatesSubsidiariesAssociatesAndJointVentures" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Investments in subsidiaries</link:label>
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    <link:label id="lab_us-gaap_OtherRestructuringMember_48c3dc00-1e62-40c0-bdaf-ad13608e6338_terseLabel_en-US" xlink:label="lab_us-gaap_OtherRestructuringMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Other costs</link:label>
    <link:label id="lab_us-gaap_OtherRestructuringMember_label_en-US" xlink:label="lab_us-gaap_OtherRestructuringMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Other Restructuring [Member]</link:label>
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    <link:label id="lab_us-gaap_NetCashProvidedByUsedInInvestingActivities_c6f2f3f2-f352-4632-a82a-98c89a1c4c5a_totalLabel_en-US" xlink:label="lab_us-gaap_NetCashProvidedByUsedInInvestingActivities" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Net cash used in investing activities</link:label>
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    <link:label id="lab_ecd_AggtChngPnsnValInSummryCompstnTblForAplblYrMember_terseLabel_en-US" xlink:label="lab_ecd_AggtChngPnsnValInSummryCompstnTblForAplblYrMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Aggregate Change in Present Value of Accumulated Benefit for All Pension Plans Reported in Summary Compensation Table</link:label>
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    <link:label id="lab_us-gaap_PurchaseObligationDueInNextTwelveMonths_8aa3e748-5af7-4434-a18c-594ad13e8eeb_terseLabel_en-US" xlink:label="lab_us-gaap_PurchaseObligationDueInNextTwelveMonths" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">2026</link:label>
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    <link:label id="lab_root_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseLossAdjustmentExpenseNet_9f125ba3-531e-4a8b-8129-77eff4a7408b_terseLabel_en-US" xlink:label="lab_root_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseLossAdjustmentExpenseNet" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">ULAE reserves&#8212;net of reinsurance</link:label>
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    <link:label id="lab_us-gaap_InterestPaidNet_64fe4b2e-22b7-4b23-b387-44ce19704d28_verboseLabel_en-US" xlink:label="lab_us-gaap_InterestPaidNet" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Interest paid</link:label>
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    <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" xml:lang="en-US">Plan Name [Domain]</link:label>
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    <link:label id="lab_us-gaap_CarryingReportedAmountFairValueDisclosureMember_6208d7b4-1e76-4ea6-adad-ae1ea379fe9f_terseLabel_en-US" xlink:label="lab_us-gaap_CarryingReportedAmountFairValueDisclosureMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" xml:lang="en-US">Reported Value Measurement [Member]</link:label>
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    <link:label id="lab_root_OtherInsuranceExpenseMember_8bfb0f44-ea2c-4237-9f05-c52fb05df081_terseLabel_en-US" xlink:label="lab_root_OtherInsuranceExpenseMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Other insurance expense</link:label>
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    <link:label id="lab_us-gaap_EmployeeServiceShareBasedCompensationNonvestedAwardsTotalCompensationCostNotYetRecognizedPeriodForRecognition1_1b0657ad-5167-4676-8b91-253b946a921e_terseLabel_en-US" xlink:label="lab_us-gaap_EmployeeServiceShareBasedCompensationNonvestedAwardsTotalCompensationCostNotYetRecognizedPeriodForRecognition1" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Remaining weighted-average period cost is expected to be recognized (in years)</link:label>
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    <link:label id="lab_us-gaap_DeferredTaxAssetsValuationAllowance_f21a001e-a315-45f3-ba8c-f04f3aea9b8a_terseLabel_en-US" xlink:label="lab_us-gaap_DeferredTaxAssetsValuationAllowance" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Valuation allowance</link:label>
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    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_CompActuallyPaidVsTotalShareholderRtnTextBlock" xlink:to="lab_ecd_CompActuallyPaidVsTotalShareholderRtnTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LesseeLeasesPolicyTextBlock_c335bdfe-f58d-4647-88df-b9fb0bb2633a_terseLabel_en-US" xlink:label="lab_us-gaap_LesseeLeasesPolicyTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Leases</link:label>
    <link:label id="lab_us-gaap_LesseeLeasesPolicyTextBlock_label_en-US" xlink:label="lab_us-gaap_LesseeLeasesPolicyTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Lessee, Leases [Policy Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LesseeLeasesPolicyTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_LesseeLeasesPolicyTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LesseeLeasesPolicyTextBlock" xlink:to="lab_us-gaap_LesseeLeasesPolicyTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_root_DebtInstrumentInterestRatePrepaymentPremium_6485ddab-7bd7-4482-a67d-3f34f186b54f_terseLabel_en-US" xlink:label="lab_root_DebtInstrumentInterestRatePrepaymentPremium" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Debt instrument, prepayment premium</link:label>
    <link:label id="lab_root_DebtInstrumentInterestRatePrepaymentPremium_label_en-US" xlink:label="lab_root_DebtInstrumentInterestRatePrepaymentPremium" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Instrument, Interest Rate, Prepayment Premium</link:label>
    <link:label id="lab_root_DebtInstrumentInterestRatePrepaymentPremium_documentation_en-US" xlink:label="lab_root_DebtInstrumentInterestRatePrepaymentPremium" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Debt Instrument, Interest Rate, Prepayment Premium</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_root_DebtInstrumentInterestRatePrepaymentPremium" xlink:href="root-20251231.xsd#root_DebtInstrumentInterestRatePrepaymentPremium"/>
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    <link:label id="lab_root_TermLoanCMember_d4dab5fb-d0e3-47ac-80f6-80f1fa0d43d5_terseLabel_en-US" xlink:label="lab_root_TermLoanCMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Principal balance</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" 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" xml:lang="en-US">Term Loan C</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_root_TermLoanCMember" xlink:href="root-20251231.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_us-gaap_DirectPremiumsWritten_f01d55a2-d121-42b4-bee1-3956969a0f4b_verboseLabel_en-US" xlink:label="lab_us-gaap_DirectPremiumsWritten" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" 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" 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/2025/elts/us-gaap-2025.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_IncomeTaxReconciliationForeignIncomeTaxRateDifferential_019c715e-11b0-76c3-a197-53289e379149_terseLabel_en-US" xlink:label="lab_us-gaap_IncomeTaxReconciliationForeignIncomeTaxRateDifferential" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Foreign rate differential</link:label>
    <link:label id="lab_us-gaap_IncomeTaxReconciliationForeignIncomeTaxRateDifferential_label_en-US" xlink:label="lab_us-gaap_IncomeTaxReconciliationForeignIncomeTaxRateDifferential" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Effective Income Tax Rate Reconciliation, Foreign Income Tax Rate Differential, Amount</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncomeTaxReconciliationForeignIncomeTaxRateDifferential" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_IncomeTaxReconciliationForeignIncomeTaxRateDifferential"/>
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    <link:label id="lab_ecd_TrdArrDuration_terseLabel_en-US" xlink:label="lab_ecd_TrdArrDuration" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Arrangement Duration</link:label>
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    <link:loc xlink:type="locator" xlink:label="loc_ecd_TrdArrDuration" xlink:href="https://xbrl.sec.gov/ecd/2025/ecd-2025.xsd#ecd_TrdArrDuration"/>
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    <link:label id="lab_us-gaap_ComputerEquipmentMember_ee2aecaa-8294-49dd-990a-b49e77b09a97_terseLabel_en-US" xlink:label="lab_us-gaap_ComputerEquipmentMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Computers</link:label>
    <link:label id="lab_us-gaap_ComputerEquipmentMember_label_en-US" xlink:label="lab_us-gaap_ComputerEquipmentMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Computer Equipment [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ComputerEquipmentMember" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_ComputerEquipmentMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ComputerEquipmentMember" xlink:to="lab_us-gaap_ComputerEquipmentMember" xlink:type="arc" order="1"/>
    <link:label id="lab_root_AllOtherStatesMember_a927e005-6762-4fee-b5c7-926f0ada5055_terseLabel_en-US" xlink:label="lab_root_AllOtherStatesMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">All others states</link:label>
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    <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" xml:lang="en-US">All Other States</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_root_AllOtherStatesMember" xlink:href="root-20251231.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_root_PerformanceSharesVestingOverTwoYearsMember_9f465a08-72b2-44e2-896f-d2c3778108a7_terseLabel_en-US" xlink:label="lab_root_PerformanceSharesVestingOverTwoYearsMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Performance Shares, Vesting Over Two Years</link:label>
    <link:label id="lab_root_PerformanceSharesVestingOverTwoYearsMember_label_en-US" xlink:label="lab_root_PerformanceSharesVestingOverTwoYearsMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Performance Shares, Vesting Over Two Years [Member]</link:label>
    <link:label id="lab_root_PerformanceSharesVestingOverTwoYearsMember_documentation_en-US" xlink:label="lab_root_PerformanceSharesVestingOverTwoYearsMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Performance Shares, Vesting Over Two Years</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_root_PerformanceSharesVestingOverTwoYearsMember" xlink:href="root-20251231.xsd#root_PerformanceSharesVestingOverTwoYearsMember"/>
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    <link:label id="lab_dei_LocalPhoneNumber_970d301b-9a06-42ae-ae3e-940e4998f51e_terseLabel_en-US" xlink:label="lab_dei_LocalPhoneNumber" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2025/dei-2025.xsd#dei_LocalPhoneNumber"/>
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    <link:label id="lab_ecd_Additional402vDisclosureTextBlock_terseLabel_en-US" xlink:label="lab_ecd_Additional402vDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Additional 402(v) Disclosure</link:label>
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    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_Additional402vDisclosureTextBlock" xlink:to="lab_ecd_Additional402vDisclosureTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DisclosureOfCompensationRelatedCostsShareBasedPaymentsTextBlock_a884c37f-ad55-4432-8aac-af12f8d8d982_terseLabel_en-US" xlink:label="lab_us-gaap_DisclosureOfCompensationRelatedCostsShareBasedPaymentsTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2025/elts/us-gaap-2025.xsd#us-gaap_DisclosureOfCompensationRelatedCostsShareBasedPaymentsTextBlock"/>
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    <link:label id="lab_root_TemporaryEquityAndStockholdersEquityNoteDisclosureTextBlock_ebe18113-a81d-4cff-b5c1-a399d3285519_terseLabel_en-US" xlink:label="lab_root_TemporaryEquityAndStockholdersEquityNoteDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">CAPITAL STOCK</link:label>
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    <link:label id="lab_root_TemporaryEquityAndStockholdersEquityNoteDisclosureTextBlock_documentation_en-US" xlink:label="lab_root_TemporaryEquityAndStockholdersEquityNoteDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Temporary Equity And Stockholders' Equity Note Disclosure</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_root_TemporaryEquityAndStockholdersEquityNoteDisclosureTextBlock" xlink:href="root-20251231.xsd#root_TemporaryEquityAndStockholdersEquityNoteDisclosureTextBlock"/>
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    <link:label id="lab_us-gaap_AssetsAbstract_967f1923-e920-4a3e-93bc-d64c34ca5a4a_terseLabel_en-US" xlink:label="lab_us-gaap_AssetsAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" xml:lang="en-US">Assets [Abstract]</link:label>
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    <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_ecd_UndrlygSecurityMktPriceChngPct_terseLabel_en-US" xlink:label="lab_ecd_UndrlygSecurityMktPriceChngPct" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Underlying Security Market Price Change</link:label>
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    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_UndrlygSecurityMktPriceChngPct" xlink:to="lab_ecd_UndrlygSecurityMktPriceChngPct" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DebtInstrumentAxis_4ffef2ce-dd80-4d16-a631-3fd9aa4d0d29_terseLabel_en-US" xlink:label="lab_us-gaap_DebtInstrumentAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2025/elts/us-gaap-2025.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_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsForfeituresWeightedAverageGrantDateFairValue_53ac815a-2690-41e5-8c6d-0823c1b4c46e_terseLabel_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsForfeituresWeightedAverageGrantDateFairValue" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Forfeited, expired or canceled (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" 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>
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    <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_FairValueDisclosuresTextBlock_5e3570b6-e36c-4c4a-9349-93d6c0774f8e_terseLabel_en-US" xlink:label="lab_us-gaap_FairValueDisclosuresTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2025/elts/us-gaap-2025.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_us-gaap_GainsLossesOnExtinguishmentOfDebt_e0a84dbf-195d-4b63-9fdd-494a6321cd90_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_GainsLossesOnExtinguishmentOfDebt" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Loss on extinguishment of debt</link:label>
    <link:label id="lab_us-gaap_GainsLossesOnExtinguishmentOfDebt_label_en-US" xlink:label="lab_us-gaap_GainsLossesOnExtinguishmentOfDebt" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Gain (Loss) on Extinguishment of Debt</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_GainsLossesOnExtinguishmentOfDebt" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_GainsLossesOnExtinguishmentOfDebt"/>
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    <link:label id="lab_us-gaap_StockholdersEquityAbstract_62b67c86-b763-4355-823e-ffdbc0af1b21_terseLabel_en-US" xlink:label="lab_us-gaap_StockholdersEquityAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Stockholders&#8217; equity:</link:label>
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    <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" xml:lang="en-US">Equity, Attributable to Parent [Abstract]</link:label>
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    <link:label id="lab_us-gaap_SharebasedCompensationArrangementBySharebasedPaymentAwardAwardVestingRightsPercentage_label_en-US" xlink:label="lab_us-gaap_SharebasedCompensationArrangementBySharebasedPaymentAwardAwardVestingRightsPercentage" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Share-Based Compensation Arrangement by Share-Based Payment Award, Award Vesting Rights, Percentage</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SharebasedCompensationArrangementBySharebasedPaymentAwardAwardVestingRightsPercentage" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_SharebasedCompensationArrangementBySharebasedPaymentAwardAwardVestingRightsPercentage"/>
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    <link:label id="lab_srt_ScheduleOfEquityMethodInvestmentEquityMethodInvesteeNameAxis_707886c4-9dbb-48b6-a290-f9edbabea208_terseLabel_en-US" xlink:label="lab_srt_ScheduleOfEquityMethodInvestmentEquityMethodInvesteeNameAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Investment, Name [Axis]</link:label>
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    <link:loc xlink:type="locator" xlink:label="loc_srt_ScheduleOfEquityMethodInvestmentEquityMethodInvesteeNameAxis" xlink:href="https://xbrl.fasb.org/srt/2025/elts/srt-2025.xsd#srt_ScheduleOfEquityMethodInvestmentEquityMethodInvesteeNameAxis"/>
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    <link:label id="lab_dei_EntityVoluntaryFilers_ea78b6e8-579a-4082-8f76-edede609c2bb_terseLabel_en-US" xlink:label="lab_dei_EntityVoluntaryFilers" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Entity Voluntary Filers</link:label>
    <link:label id="lab_dei_EntityVoluntaryFilers_label_en-US" xlink:label="lab_dei_EntityVoluntaryFilers" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Entity Voluntary Filers</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_EntityVoluntaryFilers" xlink:href="https://xbrl.sec.gov/dei/2025/dei-2025.xsd#dei_EntityVoluntaryFilers"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_EntityVoluntaryFilers" xlink:to="lab_dei_EntityVoluntaryFilers" xlink:type="arc" order="1"/>
    <link:label id="lab_root_AlexanderTimmMember_label_en-US" xlink:label="lab_root_AlexanderTimmMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Alexander Timm [Member]</link:label>
    <link:label id="lab_root_AlexanderTimmMember_documentation_en-US" xlink:label="lab_root_AlexanderTimmMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Alexander Timm</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_root_AlexanderTimmMember" xlink:href="root-20251231.xsd#root_AlexanderTimmMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_root_AlexanderTimmMember" xlink:to="lab_root_AlexanderTimmMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ShortdurationInsuranceContractsAccidentYearDomain_249a707b-78ec-4de9-aa18-b46d14aa006e_terseLabel_en-US" xlink:label="lab_us-gaap_ShortdurationInsuranceContractsAccidentYearDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Short-duration Insurance Contracts, Accident Year [Domain]</link:label>
    <link:label id="lab_us-gaap_ShortdurationInsuranceContractsAccidentYearDomain_label_en-US" xlink:label="lab_us-gaap_ShortdurationInsuranceContractsAccidentYearDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Short-Duration Insurance Contracts, Accident Year [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShortdurationInsuranceContractsAccidentYearDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_ShortdurationInsuranceContractsAccidentYearDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ShortdurationInsuranceContractsAccidentYearDomain" xlink:to="lab_us-gaap_ShortdurationInsuranceContractsAccidentYearDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_root_UnaffiliatedTexasCountyMutualInsuranceCompanyMember_1a7d9a42-2310-4ada-971b-ec9836c5bdab_terseLabel_en-US" xlink:label="lab_root_UnaffiliatedTexasCountyMutualInsuranceCompanyMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Unaffiliated Texas County Mutual Insurance Company</link:label>
    <link:label id="lab_root_UnaffiliatedTexasCountyMutualInsuranceCompanyMember_label_en-US" xlink:label="lab_root_UnaffiliatedTexasCountyMutualInsuranceCompanyMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Unaffiliated Texas County Mutual Insurance Company [Member]</link:label>
    <link:label id="lab_root_UnaffiliatedTexasCountyMutualInsuranceCompanyMember_documentation_en-US" xlink:label="lab_root_UnaffiliatedTexasCountyMutualInsuranceCompanyMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Unaffiliated Texas County Mutual Insurance Company</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_root_UnaffiliatedTexasCountyMutualInsuranceCompanyMember" xlink:href="root-20251231.xsd#root_UnaffiliatedTexasCountyMutualInsuranceCompanyMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_root_UnaffiliatedTexasCountyMutualInsuranceCompanyMember" xlink:to="lab_root_UnaffiliatedTexasCountyMutualInsuranceCompanyMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DepreciationAmortizationAndAccretionNet_e20d4a7f-d5fc-4a16-821f-11342ccaab95_terseLabel_en-US" xlink:label="lab_us-gaap_DepreciationAmortizationAndAccretionNet" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2025/elts/us-gaap-2025.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_dei_EntityRegistrantName_ae2ec629-52ce-4bc3-a239-2a989608ccb4_terseLabel_en-US" xlink:label="lab_dei_EntityRegistrantName" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2025/dei-2025.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_root_PerformanceSharesVestingOverThreeYearsMember_c7d3f0c9-a5c3-4ed6-9a8f-cab0919abc37_terseLabel_en-US" xlink:label="lab_root_PerformanceSharesVestingOverThreeYearsMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Performance Shares, Vesting Over Three Years</link:label>
    <link:label id="lab_root_PerformanceSharesVestingOverThreeYearsMember_label_en-US" xlink:label="lab_root_PerformanceSharesVestingOverThreeYearsMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Performance Shares, Vesting Over Three Years [Member]</link:label>
    <link:label id="lab_root_PerformanceSharesVestingOverThreeYearsMember_documentation_en-US" xlink:label="lab_root_PerformanceSharesVestingOverThreeYearsMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Performance Shares, Vesting Over Three Years</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_root_PerformanceSharesVestingOverThreeYearsMember" xlink:href="root-20251231.xsd#root_PerformanceSharesVestingOverThreeYearsMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_root_PerformanceSharesVestingOverThreeYearsMember" xlink:to="lab_root_PerformanceSharesVestingOverThreeYearsMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_TemporaryEquitySharesOutstanding_71d559d7-9b2c-4eff-adee-4291d64194fa_periodStartLabel_en-US" xlink:label="lab_us-gaap_TemporaryEquitySharesOutstanding" xlink:role="http://www.xbrl.org/2003/role/periodStartLabel" xlink:type="resource" xml:lang="en-US">Beginning balance (in shares)</link:label>
    <link:label id="lab_us-gaap_TemporaryEquitySharesOutstanding_711c9b8b-4326-4317-aa7d-fb180ce6fc66_periodEndLabel_en-US" xlink:label="lab_us-gaap_TemporaryEquitySharesOutstanding" xlink:role="http://www.xbrl.org/2003/role/periodEndLabel" xlink:type="resource" 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" 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/2025/elts/us-gaap-2025.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_ecd_StkPrcOrTsrEstimationMethodTextBlock_terseLabel_en-US" xlink:label="lab_ecd_StkPrcOrTsrEstimationMethodTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Stock Price or TSR Estimation Method</link:label>
    <link:label id="lab_ecd_StkPrcOrTsrEstimationMethodTextBlock_label_en-US" xlink:label="lab_ecd_StkPrcOrTsrEstimationMethodTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Stock Price or TSR Estimation Method [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_StkPrcOrTsrEstimationMethodTextBlock" xlink:href="https://xbrl.sec.gov/ecd/2025/ecd-2025.xsd#ecd_StkPrcOrTsrEstimationMethodTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_StkPrcOrTsrEstimationMethodTextBlock" xlink:to="lab_ecd_StkPrcOrTsrEstimationMethodTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_MunicipalBondsMember_3a04a351-8b99-438a-a700-1f55b180ffef_terseLabel_en-US" xlink:label="lab_us-gaap_MunicipalBondsMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2025/elts/us-gaap-2025.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_CapitalizedComputerSoftwareAmortization1_3a136b13-3765-4db8-93f4-57c292c181bd_terseLabel_en-US" xlink:label="lab_us-gaap_CapitalizedComputerSoftwareAmortization1" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Amortization expense</link:label>
    <link:label id="lab_us-gaap_CapitalizedComputerSoftwareAmortization1_label_en-US" xlink:label="lab_us-gaap_CapitalizedComputerSoftwareAmortization1" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Capitalized Computer Software, Amortization</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CapitalizedComputerSoftwareAmortization1" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_CapitalizedComputerSoftwareAmortization1"/>
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    <link:label id="lab_us-gaap_DeferredTaxAssetsTaxDeferredExpenseReservesAndAccrualsUnearnedPremiumsReserve_3f1bd023-21b8-4b21-aa2d-736196ae6afe_terseLabel_en-US" xlink:label="lab_us-gaap_DeferredTaxAssetsTaxDeferredExpenseReservesAndAccrualsUnearnedPremiumsReserve" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Unearned premium reserves</link:label>
    <link:label id="lab_us-gaap_DeferredTaxAssetsTaxDeferredExpenseReservesAndAccrualsUnearnedPremiumsReserve_label_en-US" xlink:label="lab_us-gaap_DeferredTaxAssetsTaxDeferredExpenseReservesAndAccrualsUnearnedPremiumsReserve" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Deferred Tax Assets, Tax Deferred Expense, Reserves and Accruals, Unearned Premiums Reserve</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DeferredTaxAssetsTaxDeferredExpenseReservesAndAccrualsUnearnedPremiumsReserve" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_DeferredTaxAssetsTaxDeferredExpenseReservesAndAccrualsUnearnedPremiumsReserve"/>
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    <link:label id="lab_root_CreditRatingConcentrationRiskMember_acbc5a0c-498e-4fd6-9a71-5e489c06f895_terseLabel_en-US" xlink:label="lab_root_CreditRatingConcentrationRiskMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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" xml:lang="en-US">Credit Rating Concentration Risk</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_root_CreditRatingConcentrationRiskMember" xlink:href="root-20251231.xsd#root_CreditRatingConcentrationRiskMember"/>
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    <link:label id="lab_us-gaap_AssetsFairValueDisclosure_a0d97718-2057-401f-895a-39fa19782e16_totalLabel_en-US" xlink:label="lab_us-gaap_AssetsFairValueDisclosure" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Total assets at fair value</link:label>
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    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AssetsFairValueDisclosure" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_AssetsFairValueDisclosure"/>
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    <link:label id="lab_us-gaap_DeferredTaxAssetsOperatingLossCarryforwardsStateAndLocal_7de9cd50-abed-4395-8679-c86375eb108c_terseLabel_en-US" xlink:label="lab_us-gaap_DeferredTaxAssetsOperatingLossCarryforwardsStateAndLocal" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">State net operating loss carryforward</link:label>
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    <link:label id="lab_srt_ScheduleOfValuationAndQualifyingAccountsDisclosureTextBlock_729cec4d-88b3-4471-ae7d-be2a09e0e78f_terseLabel_en-US" xlink:label="lab_srt_ScheduleOfValuationAndQualifyingAccountsDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Schedule V: Valuation and Qualifying Accounts</link:label>
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    <link:label id="lab_stpr_CA_eac88631-36d9-40ac-b22a-e48e380a9644_terseLabel_en-US" xlink:label="lab_stpr_CA" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">California</link:label>
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    <link:label id="lab_root_LossAndLossAdjustmentExpenseMember_520cc1b0-9f6c-483f-878e-c67e9c521a4d_terseLabel_en-US" xlink:label="lab_root_LossAndLossAdjustmentExpenseMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Loss and Loss Adjustment Expenses</link:label>
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    <link:label id="lab_root_LossAndLossAdjustmentExpenseMember_documentation_en-US" xlink:label="lab_root_LossAndLossAdjustmentExpenseMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Loss And Loss Adjustment Expense</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_root_LossAndLossAdjustmentExpenseMember" xlink:href="root-20251231.xsd#root_LossAndLossAdjustmentExpenseMember"/>
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    <link:label id="lab_ecd_AllIndividualsMember_terseLabel_en-US" xlink:label="lab_ecd_AllIndividualsMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">All Individuals</link:label>
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    <link:loc xlink:type="locator" xlink:label="loc_ecd_AllIndividualsMember" xlink:href="https://xbrl.sec.gov/ecd/2025/ecd-2025.xsd#ecd_AllIndividualsMember"/>
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    <link:label id="lab_us-gaap_LongtermDebtTypeDomain_8d96225b-6400-4d4d-94b2-b7c070ba7aa6_terseLabel_en-US" xlink:label="lab_us-gaap_LongtermDebtTypeDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Long-term Debt, Type [Domain]</link:label>
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    <link:label id="lab_us-gaap_PaymentsToAcquirePropertyPlantAndEquipment_cc8c2ce6-40a9-4a04-a45e-9b54e70eaf3b_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_PaymentsToAcquirePropertyPlantAndEquipment" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Purchases of fixed assets</link:label>
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    <link:label id="lab_ecd_ForgoneRecoveryIndName_terseLabel_en-US" xlink:label="lab_ecd_ForgoneRecoveryIndName" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Name</link:label>
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    <link:label id="lab_root_RootInsuranceCompanyMember_45f5fe21-6bda-4ca5-9e27-2da8d57dc52e_terseLabel_en-US" xlink:label="lab_root_RootInsuranceCompanyMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Root Insurance Company</link:label>
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    <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" xml:lang="en-US">Root Insurance Company</link:label>
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    <link:label id="lab_ecd_ChngInFrValOfOutsdngAndUnvstdEqtyAwrdsGrntdInPrrYrsMember_terseLabel_en-US" xlink:label="lab_ecd_ChngInFrValOfOutsdngAndUnvstdEqtyAwrdsGrntdInPrrYrsMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Year-over-Year Change in Fair Value of Equity Awards Granted in Prior Years That are Outstanding and Unvested</link:label>
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    <link:label id="lab_us-gaap_AdjustmentOfWarrantsGrantedForServices_a1cd9dd6-37c2-4264-8aed-20cf8ec3ba87_terseLabel_en-US" xlink:label="lab_us-gaap_AdjustmentOfWarrantsGrantedForServices" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Warrant compensation expense</link:label>
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    <link:label id="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesSingleMaturityDateAmortizedCostBasisAbstract_7e2fbd9f-2917-4d55-89c7-79335b670cfa_terseLabel_en-US" xlink:label="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesSingleMaturityDateAmortizedCostBasisAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Amortized Cost</link:label>
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    <link:label id="lab_us-gaap_ShortdurationInsuranceContractsNumberOfReportedClaims_468b98be-f220-43c4-868a-4690c2621d4b_terseLabel_en-US" xlink:label="lab_us-gaap_ShortdurationInsuranceContractsNumberOfReportedClaims" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Reported claims</link:label>
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    <link:label id="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseNet_aef9d39d-930a-49df-92fa-edd781a49017_totalLabel_en-US" xlink:label="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseNet" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Net loss and LAE reserves, January 1</link:label>
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    <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" xml:lang="en-US">Net Income (Loss) Attributable to Parent</link:label>
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    <link:label id="lab_root_ShareBasedPaymentArrangementTrancheFiveMember_d7023e28-548c-4dd6-a691-8dc70de028da_terseLabel_en-US" xlink:label="lab_root_ShareBasedPaymentArrangementTrancheFiveMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Tranche 5</link:label>
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    <link:label id="lab_stpr_GA_1d8c9f53-e3c1-42c9-b544-84a2f6ee1c76_terseLabel_en-US" xlink:label="lab_stpr_GA" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Georgia</link:label>
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    <link:label id="lab_us-gaap_ScheduleOfEffectiveIncomeTaxRateReconciliationTableTextBlock_4d1a2f9b-c3ed-492b-b049-d2496a360cec_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfEffectiveIncomeTaxRateReconciliationTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Schedule of Effective Income Tax Reconciliation</link:label>
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    <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_ecd_TrdArrAdoptionDate_terseLabel_en-US" xlink:label="lab_ecd_TrdArrAdoptionDate" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Adoption Date</link:label>
    <link:label id="lab_ecd_TrdArrAdoptionDate_label_en-US" xlink:label="lab_ecd_TrdArrAdoptionDate" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Trading Arrangement Adoption Date</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_TrdArrAdoptionDate" xlink:href="https://xbrl.sec.gov/ecd/2025/ecd-2025.xsd#ecd_TrdArrAdoptionDate"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_TrdArrAdoptionDate" xlink:to="lab_ecd_TrdArrAdoptionDate" xlink:type="arc" order="1"/>
    <link:label id="lab_root_StandardPoorsAPlusAAMinusRatingMember_db5f56d5-4cd5-4e77-81ec-88bb4a4325b6_terseLabel_en-US" xlink:label="lab_root_StandardPoorsAPlusAAMinusRatingMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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" 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-20251231.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_us-gaap_SellingGeneralAndAdministrativeExpensesPolicyTextBlock_b2dfb097-0006-437f-b3c1-20bcc2e083f0_terseLabel_en-US" xlink:label="lab_us-gaap_SellingGeneralAndAdministrativeExpensesPolicyTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Sales and Marketing</link:label>
    <link:label id="lab_us-gaap_SellingGeneralAndAdministrativeExpensesPolicyTextBlock_73e1ca1e-ea51-45e5-8bbe-780020de0923_verboseLabel_en-US" xlink:label="lab_us-gaap_SellingGeneralAndAdministrativeExpensesPolicyTextBlock" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">General and Administrative</link:label>
    <link:label id="lab_us-gaap_SellingGeneralAndAdministrativeExpensesPolicyTextBlock_label_en-US" xlink:label="lab_us-gaap_SellingGeneralAndAdministrativeExpensesPolicyTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Selling, General and Administrative Expenses, Policy [Policy Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SellingGeneralAndAdministrativeExpensesPolicyTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_SellingGeneralAndAdministrativeExpensesPolicyTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_SellingGeneralAndAdministrativeExpensesPolicyTextBlock" xlink:to="lab_us-gaap_SellingGeneralAndAdministrativeExpensesPolicyTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_OperatingIncomeLoss_7d3a46c9-1ba5-428e-a31d-1acbe35d47d2_totalLabel_en-US" xlink:label="lab_us-gaap_OperatingIncomeLoss" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Operating income (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" 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/2025/elts/us-gaap-2025.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_stpr_FL_d6f406b1-e64e-4309-9c46-82efc65141ef_terseLabel_en-US" xlink:label="lab_stpr_FL" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Florida</link:label>
    <link:label id="lab_stpr_FL_label_en-US" xlink:label="lab_stpr_FL" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">FLORIDA</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_stpr_FL" xlink:href="https://xbrl.sec.gov/stpr/2025/stpr-2025.xsd#stpr_FL"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_stpr_FL" xlink:to="lab_stpr_FL" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_RetainedEarningsAccumulatedDeficit_b035ee4e-85d4-4c0c-82ad-2a0bd2e2afd1_terseLabel_en-US" xlink:label="lab_us-gaap_RetainedEarningsAccumulatedDeficit" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Accumulated loss</link:label>
    <link:label id="lab_us-gaap_RetainedEarningsAccumulatedDeficit_ddfa6dc3-a2ee-43db-834c-0d7f5d0bd388_verboseLabel_en-US" xlink:label="lab_us-gaap_RetainedEarningsAccumulatedDeficit" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" 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" 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/2025/elts/us-gaap-2025.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_root_ShareBasedPaymentArrangementTrancheFourMember_01f8addf-a846-4c68-8002-7c685835e03d_terseLabel_en-US" xlink:label="lab_root_ShareBasedPaymentArrangementTrancheFourMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Tranche 4</link:label>
    <link:label id="lab_root_ShareBasedPaymentArrangementTrancheFourMember_label_en-US" xlink:label="lab_root_ShareBasedPaymentArrangementTrancheFourMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Share-Based Payment Arrangement, Tranche Four [Member]</link:label>
    <link:label id="lab_root_ShareBasedPaymentArrangementTrancheFourMember_documentation_en-US" xlink:label="lab_root_ShareBasedPaymentArrangementTrancheFourMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Share-Based Payment Arrangement, Tranche Four</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_root_ShareBasedPaymentArrangementTrancheFourMember" xlink:href="root-20251231.xsd#root_ShareBasedPaymentArrangementTrancheFourMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_root_ShareBasedPaymentArrangementTrancheFourMember" xlink:to="lab_root_ShareBasedPaymentArrangementTrancheFourMember" xlink:type="arc" order="1"/>
    <link:label id="lab_root_ReinsuranceRecoverableProvisionForLossCorridor_aa56132b-7ca1-4bd1-8279-e30677a59e40_terseLabel_en-US" xlink:label="lab_root_ReinsuranceRecoverableProvisionForLossCorridor" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Provision for loss corridor</link:label>
    <link:label id="lab_root_ReinsuranceRecoverableProvisionForLossCorridor_label_en-US" xlink:label="lab_root_ReinsuranceRecoverableProvisionForLossCorridor" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Reinsurance Recoverable, Provision For Loss Corridor</link:label>
    <link:label id="lab_root_ReinsuranceRecoverableProvisionForLossCorridor_documentation_en-US" xlink:label="lab_root_ReinsuranceRecoverableProvisionForLossCorridor" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Reinsurance Recoverable, Provision For Loss Corridor</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_root_ReinsuranceRecoverableProvisionForLossCorridor" xlink:href="root-20251231.xsd#root_ReinsuranceRecoverableProvisionForLossCorridor"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_root_ReinsuranceRecoverableProvisionForLossCorridor" xlink:to="lab_root_ReinsuranceRecoverableProvisionForLossCorridor" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ProceedsFromIssuanceOfConvertiblePreferredStock_b22f6ed8-17f0-46ae-abea-bbf7c841385a_terseLabel_en-US" xlink:label="lab_us-gaap_ProceedsFromIssuanceOfConvertiblePreferredStock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Proceeds from issuance of convertible stock</link:label>
    <link:label id="lab_us-gaap_ProceedsFromIssuanceOfConvertiblePreferredStock_label_en-US" xlink:label="lab_us-gaap_ProceedsFromIssuanceOfConvertiblePreferredStock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Proceeds from Issuance of Convertible Preferred Stock</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ProceedsFromIssuanceOfConvertiblePreferredStock" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_ProceedsFromIssuanceOfConvertiblePreferredStock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ProceedsFromIssuanceOfConvertiblePreferredStock" xlink:to="lab_us-gaap_ProceedsFromIssuanceOfConvertiblePreferredStock" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_YrEndFrValOfEqtyAwrdsGrntdInCvrdYrOutsdngAndUnvstdMember_terseLabel_en-US" xlink:label="lab_ecd_YrEndFrValOfEqtyAwrdsGrntdInCvrdYrOutsdngAndUnvstdMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Year-end Fair Value of Equity Awards Granted in Covered Year that are Outstanding and Unvested</link:label>
    <link:label id="lab_ecd_YrEndFrValOfEqtyAwrdsGrntdInCvrdYrOutsdngAndUnvstdMember_label_en-US" xlink:label="lab_ecd_YrEndFrValOfEqtyAwrdsGrntdInCvrdYrOutsdngAndUnvstdMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Year-end Fair Value of Equity Awards Granted in Covered Year that are Outstanding and Unvested [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_YrEndFrValOfEqtyAwrdsGrntdInCvrdYrOutsdngAndUnvstdMember" xlink:href="https://xbrl.sec.gov/ecd/2025/ecd-2025.xsd#ecd_YrEndFrValOfEqtyAwrdsGrntdInCvrdYrOutsdngAndUnvstdMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_YrEndFrValOfEqtyAwrdsGrntdInCvrdYrOutsdngAndUnvstdMember" xlink:to="lab_ecd_YrEndFrValOfEqtyAwrdsGrntdInCvrdYrOutsdngAndUnvstdMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ImpairmentOfIntangibleAssetsIndefinitelivedExcludingGoodwill_b209753a-c4b0-4a2f-9db4-5133dc952fef_terseLabel_en-US" xlink:label="lab_us-gaap_ImpairmentOfIntangibleAssetsIndefinitelivedExcludingGoodwill" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Impairment of intangible assets</link:label>
    <link:label id="lab_us-gaap_ImpairmentOfIntangibleAssetsIndefinitelivedExcludingGoodwill_label_en-US" xlink:label="lab_us-gaap_ImpairmentOfIntangibleAssetsIndefinitelivedExcludingGoodwill" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Impairment of Intangible Assets, Indefinite-Lived (Excluding Goodwill)</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ImpairmentOfIntangibleAssetsIndefinitelivedExcludingGoodwill" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_ImpairmentOfIntangibleAssetsIndefinitelivedExcludingGoodwill"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ImpairmentOfIntangibleAssetsIndefinitelivedExcludingGoodwill" xlink:to="lab_us-gaap_ImpairmentOfIntangibleAssetsIndefinitelivedExcludingGoodwill" xlink:type="arc" order="1"/>
    <link:label id="lab_root_ScheduleOfCapitalizedComputerSoftwareTableTextBlock_161a3605-9e46-4a76-a187-4f327e1c93af_terseLabel_en-US" xlink:label="lab_root_ScheduleOfCapitalizedComputerSoftwareTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Schedule of Internally Developed Software</link:label>
    <link:label id="lab_root_ScheduleOfCapitalizedComputerSoftwareTableTextBlock_label_en-US" xlink:label="lab_root_ScheduleOfCapitalizedComputerSoftwareTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Schedule Of Capitalized Computer Software [Table Text Block]</link:label>
    <link:label id="lab_root_ScheduleOfCapitalizedComputerSoftwareTableTextBlock_documentation_en-US" xlink:label="lab_root_ScheduleOfCapitalizedComputerSoftwareTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Schedule Of Capitalized Computer Software</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_root_ScheduleOfCapitalizedComputerSoftwareTableTextBlock" xlink:href="root-20251231.xsd#root_ScheduleOfCapitalizedComputerSoftwareTableTextBlock"/>
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    <link:label id="lab_us-gaap_StatementClassOfStockAxis_d0cbc4fc-b39e-40cc-b945-b04764b639f9_terseLabel_en-US" xlink:label="lab_us-gaap_StatementClassOfStockAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2025/elts/us-gaap-2025.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_root_ConversionOfStock_7364eb32-9629-4c4f-90db-954331776845_terseLabel_en-US" xlink:label="lab_root_ConversionOfStock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Conversion of stock (in shares)</link:label>
    <link:label id="lab_root_ConversionOfStock_label_en-US" xlink:label="lab_root_ConversionOfStock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Conversion of Stock</link:label>
    <link:label id="lab_root_ConversionOfStock_documentation_en-US" xlink:label="lab_root_ConversionOfStock" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Conversion of Stock</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_root_ConversionOfStock" xlink:href="root-20251231.xsd#root_ConversionOfStock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_root_ConversionOfStock" xlink:to="lab_root_ConversionOfStock" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_EqtyAwrdsInSummryCompstnTblForAplblYrMember_terseLabel_en-US" xlink:label="lab_ecd_EqtyAwrdsInSummryCompstnTblForAplblYrMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Aggregate Grant Date Fair Value of Equity Award Amounts Reported in Summary Compensation Table</link:label>
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    <link:loc xlink:type="locator" xlink:label="loc_ecd_EqtyAwrdsInSummryCompstnTblForAplblYrMember" xlink:href="https://xbrl.sec.gov/ecd/2025/ecd-2025.xsd#ecd_EqtyAwrdsInSummryCompstnTblForAplblYrMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_EqtyAwrdsInSummryCompstnTblForAplblYrMember" xlink:to="lab_ecd_EqtyAwrdsInSummryCompstnTblForAplblYrMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DeferredTaxLiabilitiesOther_19913fc2-a243-4dce-a1be-735f3fff509e_terseLabel_en-US" xlink:label="lab_us-gaap_DeferredTaxLiabilitiesOther" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Other</link:label>
    <link:label id="lab_us-gaap_DeferredTaxLiabilitiesOther_label_en-US" xlink:label="lab_us-gaap_DeferredTaxLiabilitiesOther" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Deferred Tax Liabilities, Other</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DeferredTaxLiabilitiesOther" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_DeferredTaxLiabilitiesOther"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DeferredTaxLiabilitiesOther" xlink:to="lab_us-gaap_DeferredTaxLiabilitiesOther" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_StatutoryAccountingPracticesStatutoryCapitalAndSurplusRequired_981e5ddf-fa88-4150-a8b3-736f85b94b94_terseLabel_en-US" xlink:label="lab_us-gaap_StatutoryAccountingPracticesStatutoryCapitalAndSurplusRequired" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Authorized control level RBC</link:label>
    <link:label id="lab_us-gaap_StatutoryAccountingPracticesStatutoryCapitalAndSurplusRequired_label_en-US" xlink:label="lab_us-gaap_StatutoryAccountingPracticesStatutoryCapitalAndSurplusRequired" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Statutory Accounting Practices, Statutory Capital and Surplus Required</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_StatutoryAccountingPracticesStatutoryCapitalAndSurplusRequired" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_StatutoryAccountingPracticesStatutoryCapitalAndSurplusRequired"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_StatutoryAccountingPracticesStatutoryCapitalAndSurplusRequired" xlink:to="lab_us-gaap_StatutoryAccountingPracticesStatutoryCapitalAndSurplusRequired" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_StatementTable_8f2bc0cf-63da-4e5a-82ff-993ad67b4522_terseLabel_en-US" xlink:label="lab_us-gaap_StatementTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2025/elts/us-gaap-2025.xsd#us-gaap_StatementTable"/>
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    <link:label id="lab_us-gaap_DeferredIncomeTaxExpenseBenefit_6ea5c1e2-d054-4575-839c-7e9bbb08a369_totalLabel_en-US" xlink:label="lab_us-gaap_DeferredIncomeTaxExpenseBenefit" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Total deferred</link:label>
    <link:label id="lab_us-gaap_DeferredIncomeTaxExpenseBenefit_label_en-US" xlink:label="lab_us-gaap_DeferredIncomeTaxExpenseBenefit" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Deferred Income Tax Expense (Benefit)</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DeferredIncomeTaxExpenseBenefit" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_DeferredIncomeTaxExpenseBenefit"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DeferredIncomeTaxExpenseBenefit" xlink:to="lab_us-gaap_DeferredIncomeTaxExpenseBenefit" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AdjustmentsToReconcileNetIncomeLossToCashProvidedByUsedInOperatingActivitiesAbstract_6f654d4b-1736-40d2-8081-f44c34b83248_terseLabel_en-US" xlink:label="lab_us-gaap_AdjustmentsToReconcileNetIncomeLossToCashProvidedByUsedInOperatingActivitiesAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Adjustments to reconcile net income (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" xml:lang="en-US">Adjustment to Reconcile Net Income to Cash Provided by (Used in) Operating Activity [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AdjustmentsToReconcileNetIncomeLossToCashProvidedByUsedInOperatingActivitiesAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_AdjustmentsToReconcileNetIncomeLossToCashProvidedByUsedInOperatingActivitiesAbstract"/>
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    <link:label id="lab_us-gaap_ShortdurationInsuranceContractsAccidentYearAxis_7bceed12-0129-4a11-b33e-3ea2a9ad6593_terseLabel_en-US" xlink:label="lab_us-gaap_ShortdurationInsuranceContractsAccidentYearAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Short-duration Insurance Contracts, Accident Year [Axis]</link:label>
    <link:label id="lab_us-gaap_ShortdurationInsuranceContractsAccidentYearAxis_label_en-US" xlink:label="lab_us-gaap_ShortdurationInsuranceContractsAccidentYearAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Short-Duration Insurance Contracts, Accident Year [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShortdurationInsuranceContractsAccidentYearAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_ShortdurationInsuranceContractsAccidentYearAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ShortdurationInsuranceContractsAccidentYearAxis" xlink:to="lab_us-gaap_ShortdurationInsuranceContractsAccidentYearAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_NetCashProvidedByUsedInFinancingActivitiesAbstract_69076b0e-e21f-4438-b417-7c70c6f355ff_terseLabel_en-US" xlink:label="lab_us-gaap_NetCashProvidedByUsedInFinancingActivitiesAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Cash flows from financing activities:</link:label>
    <link:label id="lab_us-gaap_NetCashProvidedByUsedInFinancingActivitiesAbstract_f1d1c3b4-1e0d-49e2-b16a-4b5f6850be7f_verboseLabel_en-US" xlink:label="lab_us-gaap_NetCashProvidedByUsedInFinancingActivitiesAbstract" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" 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" xml:lang="en-US">Cash Provided by (Used in) Financing Activity, Including Discontinued Operation [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NetCashProvidedByUsedInFinancingActivitiesAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.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_EffectiveIncomeTaxRateReconciliationNondeductibleExpense_d0f47790-0cd6-4683-a818-a27a8eb59352_terseLabel_en-US" xlink:label="lab_us-gaap_EffectiveIncomeTaxRateReconciliationNondeductibleExpense" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Nondeductible compensation</link:label>
    <link:label id="lab_us-gaap_EffectiveIncomeTaxRateReconciliationNondeductibleExpense_label_en-US" xlink:label="lab_us-gaap_EffectiveIncomeTaxRateReconciliationNondeductibleExpense" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Effective Income Tax Rate Reconciliation, Nondeductible Expense, Percent</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EffectiveIncomeTaxRateReconciliationNondeductibleExpense" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_EffectiveIncomeTaxRateReconciliationNondeductibleExpense"/>
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    <link:label id="lab_root_AssumedUnearnedPremiums_fc941695-8a4b-4395-8a59-a1e7142467d2_terseLabel_en-US" xlink:label="lab_root_AssumedUnearnedPremiums" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Assumed</link:label>
    <link:label id="lab_root_AssumedUnearnedPremiums_label_en-US" xlink:label="lab_root_AssumedUnearnedPremiums" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Assumed Unearned Premiums</link:label>
    <link:label id="lab_root_AssumedUnearnedPremiums_documentation_en-US" xlink:label="lab_root_AssumedUnearnedPremiums" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Assumed Unearned Premiums</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_root_AssumedUnearnedPremiums" xlink:href="root-20251231.xsd#root_AssumedUnearnedPremiums"/>
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    <link:label id="lab_root_InvestmentAgreementTermOfAgreement_3b8d2d25-839d-4a35-9246-e768f7a51cda_terseLabel_en-US" xlink:label="lab_root_InvestmentAgreementTermOfAgreement" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Investment agreement, term of agreement</link:label>
    <link:label id="lab_root_InvestmentAgreementTermOfAgreement_label_en-US" xlink:label="lab_root_InvestmentAgreementTermOfAgreement" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Investment Agreement, Term Of Agreement</link:label>
    <link:label id="lab_root_InvestmentAgreementTermOfAgreement_documentation_en-US" xlink:label="lab_root_InvestmentAgreementTermOfAgreement" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Investment Agreement, Term Of Agreement</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_root_InvestmentAgreementTermOfAgreement" xlink:href="root-20251231.xsd#root_InvestmentAgreementTermOfAgreement"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_root_InvestmentAgreementTermOfAgreement" xlink:to="lab_root_InvestmentAgreementTermOfAgreement" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_AllAdjToCompMember_terseLabel_en-US" xlink:label="lab_ecd_AllAdjToCompMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">All Adjustments to Compensation</link:label>
    <link:label id="lab_ecd_AllAdjToCompMember_label_en-US" xlink:label="lab_ecd_AllAdjToCompMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">All Adjustments to Compensation [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_AllAdjToCompMember" xlink:href="https://xbrl.sec.gov/ecd/2025/ecd-2025.xsd#ecd_AllAdjToCompMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_AllAdjToCompMember" xlink:to="lab_ecd_AllAdjToCompMember" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_AmendmentFlag_f067f3b7-33a7-4d3e-bcff-d2a78baf080a_terseLabel_en-US" xlink:label="lab_dei_AmendmentFlag" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2025/dei-2025.xsd#dei_AmendmentFlag"/>
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    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardNumberOfSharesAuthorized_e628d312-4d45-40cf-ba72-05cf38badf69_terseLabel_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardNumberOfSharesAuthorized" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Shares authorized (in shares)</link:label>
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    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardNumberOfSharesAuthorized" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardNumberOfSharesAuthorized"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardNumberOfSharesAuthorized" xlink:to="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardNumberOfSharesAuthorized" xlink:type="arc" order="1"/>
    <link:label id="lab_root_EffectiveIncomeTaxOperatingLossCarryforwardsStateAndLocalPercent_29ef3e3f-2101-4acb-bfd1-aa8f3aa18c8a_terseLabel_en-US" xlink:label="lab_root_EffectiveIncomeTaxOperatingLossCarryforwardsStateAndLocalPercent" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">State net operating loss</link:label>
    <link:label id="lab_root_EffectiveIncomeTaxOperatingLossCarryforwardsStateAndLocalPercent_label_en-US" xlink:label="lab_root_EffectiveIncomeTaxOperatingLossCarryforwardsStateAndLocalPercent" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Effective Income Tax, Operating Loss Carryforwards, State And Local, Percent</link:label>
    <link:label id="lab_root_EffectiveIncomeTaxOperatingLossCarryforwardsStateAndLocalPercent_documentation_en-US" xlink:label="lab_root_EffectiveIncomeTaxOperatingLossCarryforwardsStateAndLocalPercent" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Effective Income Tax, Operating Loss Carryforwards, State And Local, Percent</link:label>
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    <link:label id="lab_us-gaap_LiabilityForClaimsAndClaimsAdjustmentExpense_cc88b0aa-0bb8-4a25-9797-56ed230f0206_verboseLabel_en-US" xlink:label="lab_us-gaap_LiabilityForClaimsAndClaimsAdjustmentExpense" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Direct</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" 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/2025/elts/us-gaap-2025.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_ecd_TrdArrTerminationDate_terseLabel_en-US" xlink:label="lab_ecd_TrdArrTerminationDate" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Termination Date</link:label>
    <link:label id="lab_ecd_TrdArrTerminationDate_label_en-US" xlink:label="lab_ecd_TrdArrTerminationDate" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Trading Arrangement Termination Date</link:label>
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    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_TrdArrTerminationDate" xlink:to="lab_ecd_TrdArrTerminationDate" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_InsiderTrdPoliciesProcAdoptedFlag_terseLabel_en-US" xlink:label="lab_ecd_InsiderTrdPoliciesProcAdoptedFlag" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Insider Trading Policies and Procedures Adopted</link:label>
    <link:label id="lab_ecd_InsiderTrdPoliciesProcAdoptedFlag_label_en-US" xlink:label="lab_ecd_InsiderTrdPoliciesProcAdoptedFlag" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Insider Trading Policies and Procedures Adopted [Flag]</link:label>
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    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_InsiderTrdPoliciesProcAdoptedFlag" xlink:to="lab_ecd_InsiderTrdPoliciesProcAdoptedFlag" xlink:type="arc" order="1"/>
    <link:label id="lab_root_DebtSecuritiesAvailableForSaleCurrentMember_58c61bd0-07c3-4bcd-85d2-f078cbf74a71_terseLabel_en-US" xlink:label="lab_root_DebtSecuritiesAvailableForSaleCurrentMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Short-term investments</link:label>
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    <link:label id="lab_us-gaap_ShareBasedCompensationAwardTrancheThreeMember_92c50e8a-164e-46ca-807d-4ab347876330_terseLabel_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationAwardTrancheThreeMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Tranche 3</link:label>
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    <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_OperatingLeaseWeightedAverageDiscountRatePercent_06db2def-b550-44e7-a5d4-fe9f598d702b_terseLabel_en-US" xlink:label="lab_us-gaap_OperatingLeaseWeightedAverageDiscountRatePercent" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Weighted-average operating lease discount rate</link:label>
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    <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"/>
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