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

<!--XBRL Document Created with the Workiva Platform-->
<!--Copyright 2026 Workiva-->
<!--r:019feb9f-5df0-78fb-9fbb-b0d033f57524,g:315d9b13-1fdb-49a8-b9cf-13e2b2387a90-->
<link:linkbase xmlns:link="http://www.xbrl.org/2003/linkbase" xmlns:xlink="http://www.w3.org/1999/xlink" xmlns:xsi="http://www.w3.org/2001/XMLSchema-instance" xsi:schemaLocation="http://www.xbrl.org/2003/linkbase http://www.xbrl.org/2003/xbrl-linkbase-2003-12-31.xsd">
  <link:arcroleRef arcroleURI="https://xbrl.org/2023/arcrole/summation-item" xlink:type="simple" xlink:href="https://www.xbrl.org/2023/calculation-1.1.xsd#summation-item"/>
  <link:roleRef roleURI="http://www.joinroot.com/role/CONDENSEDCONSOLIDATEDBALANCESHEETSUNAUDITED" xlink:type="simple" xlink:href="root-20260930.xsd#CONDENSEDCONSOLIDATEDBALANCESHEETSUNAUDITED"/>
  <link:calculationLink xlink:role="http://www.joinroot.com/role/CONDENSEDCONSOLIDATEDBALANCESHEETSUNAUDITED" xlink:type="extended">
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_Assets_019feb9f-5f4e-7ace-b346-fbecf8948a10" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_Assets"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_Investments_019feb9f-5f4e-7d6a-9d62-85066d053b85" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_Investments"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_Assets_019feb9f-5f4e-7ace-b346-fbecf8948a10" xlink:to="loc_us-gaap_Investments_019feb9f-5f4e-7d6a-9d62-85066d053b85" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CashAndCashEquivalentsAtCarryingValue_019feb9f-5f4e-7bcd-90f3-7acb5493dd10" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_CashAndCashEquivalentsAtCarryingValue"/>
    <link:calculationArc order="2" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_Assets_019feb9f-5f4e-7ace-b346-fbecf8948a10" xlink:to="loc_us-gaap_CashAndCashEquivalentsAtCarryingValue_019feb9f-5f4e-7bcd-90f3-7acb5493dd10" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_RestrictedCashAndCashEquivalents_019feb9f-5f4e-73d2-9bff-7d97e91c5baa" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_RestrictedCashAndCashEquivalents"/>
    <link:calculationArc order="3" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_Assets_019feb9f-5f4e-7ace-b346-fbecf8948a10" xlink:to="loc_us-gaap_RestrictedCashAndCashEquivalents_019feb9f-5f4e-73d2-9bff-7d97e91c5baa" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PremiumsReceivableAtCarryingValue_019feb9f-5f4e-742f-8259-1272fad963cc" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_PremiumsReceivableAtCarryingValue"/>
    <link:calculationArc order="4" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_Assets_019feb9f-5f4e-7ace-b346-fbecf8948a10" xlink:to="loc_us-gaap_PremiumsReceivableAtCarryingValue_019feb9f-5f4e-742f-8259-1272fad963cc" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_root_ReinsurancePremiumsReceivable_019feb9f-5f4e-7ca6-aa64-6833bc1ca097" xlink:href="root-20260930.xsd#root_ReinsurancePremiumsReceivable"/>
    <link:calculationArc order="5" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_Assets_019feb9f-5f4e-7ace-b346-fbecf8948a10" xlink:to="loc_root_ReinsurancePremiumsReceivable_019feb9f-5f4e-7ca6-aa64-6833bc1ca097" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ReinsuranceRecoverablesOnPaidAndUnpaidLosses_019feb9f-5f4e-7eea-a3dc-1f0c1bc598ba" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ReinsuranceRecoverablesOnPaidAndUnpaidLosses"/>
    <link:calculationArc order="6" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_Assets_019feb9f-5f4e-7ace-b346-fbecf8948a10" xlink:to="loc_us-gaap_ReinsuranceRecoverablesOnPaidAndUnpaidLosses_019feb9f-5f4e-7eea-a3dc-1f0c1bc598ba" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DeferredPolicyAcquisitionCosts_019feb9f-5f4e-75c7-a540-7203b8eca494" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DeferredPolicyAcquisitionCosts"/>
    <link:calculationArc order="7" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_Assets_019feb9f-5f4e-7ace-b346-fbecf8948a10" xlink:to="loc_us-gaap_DeferredPolicyAcquisitionCosts_019feb9f-5f4e-75c7-a540-7203b8eca494" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OtherAssets_019feb9f-5f4e-7bdc-a6a7-92b371cf6fc0" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_OtherAssets"/>
    <link:calculationArc order="8" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_Assets_019feb9f-5f4e-7ace-b346-fbecf8948a10" xlink:to="loc_us-gaap_OtherAssets_019feb9f-5f4e-7bdc-a6a7-92b371cf6fc0" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LiabilitiesAndStockholdersEquity_019feb9f-5f4e-7e63-b84c-25e59931af49" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_LiabilitiesAndStockholdersEquity"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_Liabilities_019feb9f-5f4e-72ae-ace4-bd2f7093cc41" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_Liabilities"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_LiabilitiesAndStockholdersEquity_019feb9f-5f4e-7e63-b84c-25e59931af49" xlink:to="loc_us-gaap_Liabilities_019feb9f-5f4e-72ae-ace4-bd2f7093cc41" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_StockholdersEquity_019feb9f-5f4e-7586-aae3-4e46c45a61b9" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_StockholdersEquity"/>
    <link:calculationArc order="2" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_LiabilitiesAndStockholdersEquity_019feb9f-5f4e-7e63-b84c-25e59931af49" xlink:to="loc_us-gaap_StockholdersEquity_019feb9f-5f4e-7586-aae3-4e46c45a61b9" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CommitmentsAndContingencies_019feb9f-5f4e-7e51-9790-1ccdcf495795" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_CommitmentsAndContingencies"/>
    <link:calculationArc order="3" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_LiabilitiesAndStockholdersEquity_019feb9f-5f4e-7e63-b84c-25e59931af49" xlink:to="loc_us-gaap_CommitmentsAndContingencies_019feb9f-5f4e-7e51-9790-1ccdcf495795" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_TemporaryEquityCarryingAmountAttributableToParent_019feb9f-5f4e-78cd-9af6-9e3f3a99adb2" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_TemporaryEquityCarryingAmountAttributableToParent"/>
    <link:calculationArc order="4" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_LiabilitiesAndStockholdersEquity_019feb9f-5f4e-7e63-b84c-25e59931af49" xlink:to="loc_us-gaap_TemporaryEquityCarryingAmountAttributableToParent_019feb9f-5f4e-78cd-9af6-9e3f3a99adb2" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_StockholdersEquity_019feb9f-5f4e-797e-ac33-2b720108e4f2" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_StockholdersEquity"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AccumulatedOtherComprehensiveIncomeLossNetOfTax_019feb9f-5f4e-7d2e-b6ec-54f32f33a95a" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_AccumulatedOtherComprehensiveIncomeLossNetOfTax"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_StockholdersEquity_019feb9f-5f4e-797e-ac33-2b720108e4f2" xlink:to="loc_us-gaap_AccumulatedOtherComprehensiveIncomeLossNetOfTax_019feb9f-5f4e-7d2e-b6ec-54f32f33a95a" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_RetainedEarningsAccumulatedDeficit_019feb9f-5f4e-79bc-beab-eccd5775a217" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_RetainedEarningsAccumulatedDeficit"/>
    <link:calculationArc order="2" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_StockholdersEquity_019feb9f-5f4e-797e-ac33-2b720108e4f2" xlink:to="loc_us-gaap_RetainedEarningsAccumulatedDeficit_019feb9f-5f4e-79bc-beab-eccd5775a217" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AdditionalPaidInCapital_019feb9f-5f4e-7e5d-bb1a-aa2297601897" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_AdditionalPaidInCapital"/>
    <link:calculationArc order="3" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_StockholdersEquity_019feb9f-5f4e-797e-ac33-2b720108e4f2" xlink:to="loc_us-gaap_AdditionalPaidInCapital_019feb9f-5f4e-7e5d-bb1a-aa2297601897" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CommonStockValue_019feb9f-5f4e-710c-bb0e-6faac38dec32" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_CommonStockValue"/>
    <link:calculationArc order="4" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_StockholdersEquity_019feb9f-5f4e-797e-ac33-2b720108e4f2" xlink:to="loc_us-gaap_CommonStockValue_019feb9f-5f4e-710c-bb0e-6faac38dec32" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_Liabilities_019feb9f-5f4e-77db-97e5-b734cf62547d" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_Liabilities"/>
    <link:loc xlink:type="locator" xlink:label="loc_root_LiabilityForClaimsAndClaimsAdjustmentExpenseGross_019feb9f-5f4e-7965-b42f-fd2f247f3743" xlink:href="root-20260930.xsd#root_LiabilityForClaimsAndClaimsAdjustmentExpenseGross"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_Liabilities_019feb9f-5f4e-77db-97e5-b734cf62547d" xlink:to="loc_root_LiabilityForClaimsAndClaimsAdjustmentExpenseGross_019feb9f-5f4e-7965-b42f-fd2f247f3743" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_root_UnearnedPremiumsGross_019feb9f-5f4e-751d-bfb0-a9f2b9561ce0" xlink:href="root-20260930.xsd#root_UnearnedPremiumsGross"/>
    <link:calculationArc order="2" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_Liabilities_019feb9f-5f4e-77db-97e5-b734cf62547d" xlink:to="loc_root_UnearnedPremiumsGross_019feb9f-5f4e-751d-bfb0-a9f2b9561ce0" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LongTermDebt_019feb9f-5f4e-7cf1-9ab9-58bc3c06d4a5" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_LongTermDebt"/>
    <link:calculationArc order="3" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_Liabilities_019feb9f-5f4e-77db-97e5-b734cf62547d" xlink:to="loc_us-gaap_LongTermDebt_019feb9f-5f4e-7cf1-9ab9-58bc3c06d4a5" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_root_PremiumsPayable_019feb9f-5f4e-70a4-b27a-e6bea6a104e0" xlink:href="root-20260930.xsd#root_PremiumsPayable"/>
    <link:calculationArc order="4" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_Liabilities_019feb9f-5f4e-77db-97e5-b734cf62547d" xlink:to="loc_root_PremiumsPayable_019feb9f-5f4e-70a4-b27a-e6bea6a104e0" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AccountsPayableAndAccruedLiabilitiesCurrentAndNoncurrent_019feb9f-5f4e-7174-b0c7-9a35349c823c" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_AccountsPayableAndAccruedLiabilitiesCurrentAndNoncurrent"/>
    <link:calculationArc order="5" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_Liabilities_019feb9f-5f4e-77db-97e5-b734cf62547d" xlink:to="loc_us-gaap_AccountsPayableAndAccruedLiabilitiesCurrentAndNoncurrent_019feb9f-5f4e-7174-b0c7-9a35349c823c" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OtherLiabilities_019feb9f-5f4e-742d-99ba-b3ec502afa29" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_OtherLiabilities"/>
    <link:calculationArc order="6" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_Liabilities_019feb9f-5f4e-77db-97e5-b734cf62547d" xlink:to="loc_us-gaap_OtherLiabilities_019feb9f-5f4e-742d-99ba-b3ec502afa29" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_Investments_019feb9f-5f4e-7f39-83ad-cff0fe637c02" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_Investments"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtSecuritiesAvailableForSaleExcludingAccruedInterestNoncurrent_019feb9f-5f4e-7be7-8912-50c088b9e458" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DebtSecuritiesAvailableForSaleExcludingAccruedInterestNoncurrent"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_Investments_019feb9f-5f4e-7f39-83ad-cff0fe637c02" xlink:to="loc_us-gaap_DebtSecuritiesAvailableForSaleExcludingAccruedInterestNoncurrent_019feb9f-5f4e-7be7-8912-50c088b9e458" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtSecuritiesAvailableForSaleExcludingAccruedInterestCurrent_019feb9f-5f4e-7cef-8c46-9d7ed9c7b83a" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DebtSecuritiesAvailableForSaleExcludingAccruedInterestCurrent"/>
    <link:calculationArc order="2" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_Investments_019feb9f-5f4e-7f39-83ad-cff0fe637c02" xlink:to="loc_us-gaap_DebtSecuritiesAvailableForSaleExcludingAccruedInterestCurrent_019feb9f-5f4e-7cef-8c46-9d7ed9c7b83a" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OtherInvestments_019feb9f-5f4e-7bdd-9393-0159e8ec1538" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_OtherInvestments"/>
    <link:calculationArc order="3" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_Investments_019feb9f-5f4e-7f39-83ad-cff0fe637c02" xlink:to="loc_us-gaap_OtherInvestments_019feb9f-5f4e-7bdd-9393-0159e8ec1538" xlink:type="arc"/>
  </link:calculationLink>
  <link:roleRef roleURI="http://www.joinroot.com/role/CONDENSEDCONSOLIDATEDSTATEMENTSOFOPERATIONSANDCOMPREHENSIVEINCOMELOSSUNAUDITED" xlink:type="simple" xlink:href="root-20260930.xsd#CONDENSEDCONSOLIDATEDSTATEMENTSOFOPERATIONSANDCOMPREHENSIVEINCOMELOSSUNAUDITED"/>
  <link:calculationLink xlink:role="http://www.joinroot.com/role/CONDENSEDCONSOLIDATEDSTATEMENTSOFOPERATIONSANDCOMPREHENSIVEINCOMELOSSUNAUDITED" xlink:type="extended">
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ComprehensiveIncomeNetOfTax_019feb9f-5f4e-7917-b572-38ac4da7eefa" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ComprehensiveIncomeNetOfTax"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OtherComprehensiveIncomeUnrealizedHoldingGainLossOnSecuritiesArisingDuringPeriodNetOfTax_019feb9f-5f4e-76e0-84f4-04a18306ae79" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_OtherComprehensiveIncomeUnrealizedHoldingGainLossOnSecuritiesArisingDuringPeriodNetOfTax"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_ComprehensiveIncomeNetOfTax_019feb9f-5f4e-7917-b572-38ac4da7eefa" xlink:to="loc_us-gaap_OtherComprehensiveIncomeUnrealizedHoldingGainLossOnSecuritiesArisingDuringPeriodNetOfTax_019feb9f-5f4e-76e0-84f4-04a18306ae79" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NetIncomeLoss_019feb9f-5f4e-75eb-9edc-3975f9398de5" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_NetIncomeLoss"/>
    <link:calculationArc order="2" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_ComprehensiveIncomeNetOfTax_019feb9f-5f4e-7917-b572-38ac4da7eefa" xlink:to="loc_us-gaap_NetIncomeLoss_019feb9f-5f4e-75eb-9edc-3975f9398de5" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NetIncomeLoss_019feb9f-5f4e-7d8f-a572-29535054750e" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_NetIncomeLoss"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncomeLossFromContinuingOperationsBeforeIncomeTaxesExtraordinaryItemsNoncontrollingInterest_019feb9f-5f4e-7834-b28d-31b5a88589a1" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_IncomeLossFromContinuingOperationsBeforeIncomeTaxesExtraordinaryItemsNoncontrollingInterest"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_NetIncomeLoss_019feb9f-5f4e-7d8f-a572-29535054750e" xlink:to="loc_us-gaap_IncomeLossFromContinuingOperationsBeforeIncomeTaxesExtraordinaryItemsNoncontrollingInterest_019feb9f-5f4e-7834-b28d-31b5a88589a1" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncomeTaxExpenseBenefit_019feb9f-5f4e-78f6-a46a-6fd079db1ec4" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_IncomeTaxExpenseBenefit"/>
    <link:calculationArc order="2" weight="-1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_NetIncomeLoss_019feb9f-5f4e-7d8f-a572-29535054750e" xlink:to="loc_us-gaap_IncomeTaxExpenseBenefit_019feb9f-5f4e-78f6-a46a-6fd079db1ec4" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NetIncomeLossAvailableToCommonStockholdersBasic_019feb9f-5f4e-7f24-a20a-dcbe38cac9ff" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_NetIncomeLossAvailableToCommonStockholdersBasic"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_UndistributedEarningsLossAllocatedToParticipatingSecuritiesBasic_019feb9f-5f4e-73f9-96d8-67b45e141a43" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_UndistributedEarningsLossAllocatedToParticipatingSecuritiesBasic"/>
    <link:calculationArc order="1" weight="-1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_NetIncomeLossAvailableToCommonStockholdersBasic_019feb9f-5f4e-7f24-a20a-dcbe38cac9ff" xlink:to="loc_us-gaap_UndistributedEarningsLossAllocatedToParticipatingSecuritiesBasic_019feb9f-5f4e-73f9-96d8-67b45e141a43" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NetIncomeLoss_019feb9f-5f4e-7bc7-b8a7-b58b105679d6" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_NetIncomeLoss"/>
    <link:calculationArc order="2" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_NetIncomeLossAvailableToCommonStockholdersBasic_019feb9f-5f4e-7f24-a20a-dcbe38cac9ff" xlink:to="loc_us-gaap_NetIncomeLoss_019feb9f-5f4e-7bc7-b8a7-b58b105679d6" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncomeLossFromContinuingOperationsBeforeIncomeTaxesExtraordinaryItemsNoncontrollingInterest_019feb9f-5f4e-7df0-8a25-9db48ead09dc" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_IncomeLossFromContinuingOperationsBeforeIncomeTaxesExtraordinaryItemsNoncontrollingInterest"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OperatingIncomeLoss_019feb9f-5f4e-7bab-993e-5961863de4f3" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_OperatingIncomeLoss"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_IncomeLossFromContinuingOperationsBeforeIncomeTaxesExtraordinaryItemsNoncontrollingInterest_019feb9f-5f4e-7df0-8a25-9db48ead09dc" xlink:to="loc_us-gaap_OperatingIncomeLoss_019feb9f-5f4e-7bab-993e-5961863de4f3" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_InterestExpenseNonoperating_019feb9f-5f4e-7b35-8821-2f3eda54b3a1" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_InterestExpenseNonoperating"/>
    <link:calculationArc order="2" weight="-1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_IncomeLossFromContinuingOperationsBeforeIncomeTaxesExtraordinaryItemsNoncontrollingInterest_019feb9f-5f4e-7df0-8a25-9db48ead09dc" xlink:to="loc_us-gaap_InterestExpenseNonoperating_019feb9f-5f4e-7b35-8821-2f3eda54b3a1" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_GainsLossesOnExtinguishmentOfDebt_019feb9f-5f4e-74d4-a95e-ed50cd8b28b2" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_GainsLossesOnExtinguishmentOfDebt"/>
    <link:calculationArc order="3" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_IncomeLossFromContinuingOperationsBeforeIncomeTaxesExtraordinaryItemsNoncontrollingInterest_019feb9f-5f4e-7df0-8a25-9db48ead09dc" xlink:to="loc_us-gaap_GainsLossesOnExtinguishmentOfDebt_019feb9f-5f4e-74d4-a95e-ed50cd8b28b2" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OperatingIncomeLoss_019feb9f-5f4e-7efd-9fac-21d8ec22ac74" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_OperatingIncomeLoss"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_Revenues_019feb9f-5f4e-7417-a7af-055c6c398b32" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_Revenues"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_OperatingIncomeLoss_019feb9f-5f4e-7efd-9fac-21d8ec22ac74" xlink:to="loc_us-gaap_Revenues_019feb9f-5f4e-7417-a7af-055c6c398b32" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OperatingExpenses_019feb9f-5f4e-7061-a9fa-d081c47450db" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_OperatingExpenses"/>
    <link:calculationArc order="2" weight="-1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_OperatingIncomeLoss_019feb9f-5f4e-7efd-9fac-21d8ec22ac74" xlink:to="loc_us-gaap_OperatingExpenses_019feb9f-5f4e-7061-a9fa-d081c47450db" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_Revenues_019feb9f-5f4e-7b30-8da2-90ee4d8c9843" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_Revenues"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PremiumsEarnedNet_019feb9f-5f4e-7ef7-9640-792f7359c97c" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_PremiumsEarnedNet"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_Revenues_019feb9f-5f4e-7b30-8da2-90ee4d8c9843" xlink:to="loc_us-gaap_PremiumsEarnedNet_019feb9f-5f4e-7ef7-9640-792f7359c97c" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NetInvestmentIncome_019feb9f-5f4e-76f7-ac09-32cdc5360695" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_NetInvestmentIncome"/>
    <link:calculationArc order="2" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_Revenues_019feb9f-5f4e-7b30-8da2-90ee4d8c9843" xlink:to="loc_us-gaap_NetInvestmentIncome_019feb9f-5f4e-76f7-ac09-32cdc5360695" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_GainLossOnInvestments_019feb9f-5f4e-7660-a35f-664094d6c48f" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_GainLossOnInvestments"/>
    <link:calculationArc order="3" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_Revenues_019feb9f-5f4e-7b30-8da2-90ee4d8c9843" xlink:to="loc_us-gaap_GainLossOnInvestments_019feb9f-5f4e-7660-a35f-664094d6c48f" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FeeIncome_019feb9f-5f4e-781f-98d3-2e2290f1737d" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_FeeIncome"/>
    <link:calculationArc order="4" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_Revenues_019feb9f-5f4e-7b30-8da2-90ee4d8c9843" xlink:to="loc_us-gaap_FeeIncome_019feb9f-5f4e-781f-98d3-2e2290f1737d" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OtherIncome_019feb9f-5f4e-7721-89ce-8161ed721734" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_OtherIncome"/>
    <link:calculationArc order="5" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_Revenues_019feb9f-5f4e-7b30-8da2-90ee4d8c9843" xlink:to="loc_us-gaap_OtherIncome_019feb9f-5f4e-7721-89ce-8161ed721734" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OperatingExpenses_019feb9f-5f4e-7651-ac5b-d368317e74b6" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_OperatingExpenses"/>
    <link:loc xlink:type="locator" xlink:label="loc_root_TechnologyAndDevelopmentExpense_019feb9f-5f4e-77a5-8d4c-d9b59e545a39" xlink:href="root-20260930.xsd#root_TechnologyAndDevelopmentExpense"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_OperatingExpenses_019feb9f-5f4e-7651-ac5b-d368317e74b6" xlink:to="loc_root_TechnologyAndDevelopmentExpense_019feb9f-5f4e-77a5-8d4c-d9b59e545a39" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_GeneralAndAdministrativeExpense_019feb9f-5f4e-7daa-98a7-01463e40598f" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_GeneralAndAdministrativeExpense"/>
    <link:calculationArc order="2" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_OperatingExpenses_019feb9f-5f4e-7651-ac5b-d368317e74b6" xlink:to="loc_us-gaap_GeneralAndAdministrativeExpense_019feb9f-5f4e-7daa-98a7-01463e40598f" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_root_OtherInsuranceExpenseIncome_019feb9f-5f4e-7446-8b64-62c5ada462e2" xlink:href="root-20260930.xsd#root_OtherInsuranceExpenseIncome"/>
    <link:calculationArc order="3" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_OperatingExpenses_019feb9f-5f4e-7651-ac5b-d368317e74b6" xlink:to="loc_root_OtherInsuranceExpenseIncome_019feb9f-5f4e-7446-8b64-62c5ada462e2" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaims1_019feb9f-5f4e-70f0-8987-7c1bd558652f" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaims1"/>
    <link:calculationArc order="4" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_OperatingExpenses_019feb9f-5f4e-7651-ac5b-d368317e74b6" xlink:to="loc_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaims1_019feb9f-5f4e-70f0-8987-7c1bd558652f" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SellingAndMarketingExpense_019feb9f-5f4e-787c-acb2-a39856ecf303" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_SellingAndMarketingExpense"/>
    <link:calculationArc order="5" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_OperatingExpenses_019feb9f-5f4e-7651-ac5b-d368317e74b6" xlink:to="loc_us-gaap_SellingAndMarketingExpense_019feb9f-5f4e-787c-acb2-a39856ecf303" xlink:type="arc"/>
  </link:calculationLink>
  <link:roleRef roleURI="http://www.joinroot.com/role/CONDENSEDCONSOLIDATEDSTATEMENTSOFCASHFLOWSUNAUDITED" xlink:type="simple" xlink:href="root-20260930.xsd#CONDENSEDCONSOLIDATEDSTATEMENTSOFCASHFLOWSUNAUDITED"/>
  <link:calculationLink xlink:role="http://www.joinroot.com/role/CONDENSEDCONSOLIDATEDSTATEMENTSOFCASHFLOWSUNAUDITED" xlink:type="extended">
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NetCashProvidedByUsedInInvestingActivities_019feb9f-5f4e-7166-a268-a6cff48a51d7" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_NetCashProvidedByUsedInInvestingActivities"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PaymentsToAcquireAvailableForSaleSecuritiesDebt_019feb9f-5f4e-7fad-b775-2d06edd5312a" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_PaymentsToAcquireAvailableForSaleSecuritiesDebt"/>
    <link:calculationArc order="1" weight="-1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInInvestingActivities_019feb9f-5f4e-7166-a268-a6cff48a51d7" xlink:to="loc_us-gaap_PaymentsToAcquireAvailableForSaleSecuritiesDebt_019feb9f-5f4e-7fad-b775-2d06edd5312a" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ProceedsFromMaturitiesPrepaymentsAndCallsOfAvailableForSaleSecurities_019feb9f-5f4e-7330-ab51-f3a404ac1f9b" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ProceedsFromMaturitiesPrepaymentsAndCallsOfAvailableForSaleSecurities"/>
    <link:calculationArc order="2" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInInvestingActivities_019feb9f-5f4e-7166-a268-a6cff48a51d7" xlink:to="loc_us-gaap_ProceedsFromMaturitiesPrepaymentsAndCallsOfAvailableForSaleSecurities_019feb9f-5f4e-7330-ab51-f3a404ac1f9b" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ProceedsFromSaleOfAvailableForSaleSecuritiesDebt_019feb9f-5f4e-706b-9e3d-530b51baad6a" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ProceedsFromSaleOfAvailableForSaleSecuritiesDebt"/>
    <link:calculationArc order="3" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInInvestingActivities_019feb9f-5f4e-7166-a268-a6cff48a51d7" xlink:to="loc_us-gaap_ProceedsFromSaleOfAvailableForSaleSecuritiesDebt_019feb9f-5f4e-706b-9e3d-530b51baad6a" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PaymentsToDevelopSoftware_019feb9f-5f4e-78af-a17f-448b8cf63e4f" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_PaymentsToDevelopSoftware"/>
    <link:calculationArc order="4" weight="-1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInInvestingActivities_019feb9f-5f4e-7166-a268-a6cff48a51d7" xlink:to="loc_us-gaap_PaymentsToDevelopSoftware_019feb9f-5f4e-78af-a17f-448b8cf63e4f" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PaymentsToAcquirePropertyPlantAndEquipment_01a0c3c0-4797-7087-a609-3c4b7cc24616" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_PaymentsToAcquirePropertyPlantAndEquipment"/>
    <link:calculationArc order="5" weight="-1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInInvestingActivities_019feb9f-5f4e-7166-a268-a6cff48a51d7" xlink:to="loc_us-gaap_PaymentsToAcquirePropertyPlantAndEquipment_01a0c3c0-4797-7087-a609-3c4b7cc24616" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NetCashProvidedByUsedInFinancingActivities_019feb9f-5f4e-7918-96e6-785c93f38e66" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_NetCashProvidedByUsedInFinancingActivities"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ProceedsFromStockOptionsExercised_019feb9f-5f4e-7992-9dbf-6f20f22761b1" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ProceedsFromStockOptionsExercised"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInFinancingActivities_019feb9f-5f4e-7918-96e6-785c93f38e66" xlink:to="loc_us-gaap_ProceedsFromStockOptionsExercised_019feb9f-5f4e-7992-9dbf-6f20f22761b1" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PaymentsRelatedToTaxWithholdingForShareBasedCompensation_019feb9f-5f4e-7728-8783-6e33e1ff9e22" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_PaymentsRelatedToTaxWithholdingForShareBasedCompensation"/>
    <link:calculationArc order="2" weight="-1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInFinancingActivities_019feb9f-5f4e-7918-96e6-785c93f38e66" xlink:to="loc_us-gaap_PaymentsRelatedToTaxWithholdingForShareBasedCompensation_019feb9f-5f4e-7728-8783-6e33e1ff9e22" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PaymentsForRepurchaseOfCommonStock_019feb9f-5f4e-7d66-a1a6-bf5d618887f3" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_PaymentsForRepurchaseOfCommonStock"/>
    <link:calculationArc order="3" weight="-1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInFinancingActivities_019feb9f-5f4e-7918-96e6-785c93f38e66" xlink:to="loc_us-gaap_PaymentsForRepurchaseOfCommonStock_019feb9f-5f4e-7d66-a1a6-bf5d618887f3" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ProceedsFromDebtNetOfIssuanceCosts_019feb9f-5f4e-798d-b4d5-00ef8bf16b0f" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ProceedsFromDebtNetOfIssuanceCosts"/>
    <link:calculationArc order="4" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInFinancingActivities_019feb9f-5f4e-7918-96e6-785c93f38e66" xlink:to="loc_us-gaap_ProceedsFromDebtNetOfIssuanceCosts_019feb9f-5f4e-798d-b4d5-00ef8bf16b0f" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_RepaymentsOfLongTermDebt_019feb9f-5f4e-7880-aa85-129cf4d21e16" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_RepaymentsOfLongTermDebt"/>
    <link:calculationArc order="5" weight="-1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInFinancingActivities_019feb9f-5f4e-7918-96e6-785c93f38e66" xlink:to="loc_us-gaap_RepaymentsOfLongTermDebt_019feb9f-5f4e-7880-aa85-129cf4d21e16" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalentsPeriodIncreaseDecreaseIncludingExchangeRateEffect_019feb9f-5f4e-7906-8e37-97cd4001ecb1" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalentsPeriodIncreaseDecreaseIncludingExchangeRateEffect"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NetCashProvidedByUsedInInvestingActivities_019feb9f-5f4e-7f64-a1dd-31a1f7fdedca" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_NetCashProvidedByUsedInInvestingActivities"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalentsPeriodIncreaseDecreaseIncludingExchangeRateEffect_019feb9f-5f4e-7906-8e37-97cd4001ecb1" xlink:to="loc_us-gaap_NetCashProvidedByUsedInInvestingActivities_019feb9f-5f4e-7f64-a1dd-31a1f7fdedca" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NetCashProvidedByUsedInOperatingActivities_019feb9f-5f4e-7573-b0ad-91ef8eeb44de" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_NetCashProvidedByUsedInOperatingActivities"/>
    <link:calculationArc order="2" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalentsPeriodIncreaseDecreaseIncludingExchangeRateEffect_019feb9f-5f4e-7906-8e37-97cd4001ecb1" xlink:to="loc_us-gaap_NetCashProvidedByUsedInOperatingActivities_019feb9f-5f4e-7573-b0ad-91ef8eeb44de" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NetCashProvidedByUsedInFinancingActivities_019feb9f-5f4e-7666-9db7-e255a96aca21" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_NetCashProvidedByUsedInFinancingActivities"/>
    <link:calculationArc order="3" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalentsPeriodIncreaseDecreaseIncludingExchangeRateEffect_019feb9f-5f4e-7906-8e37-97cd4001ecb1" xlink:to="loc_us-gaap_NetCashProvidedByUsedInFinancingActivities_019feb9f-5f4e-7666-9db7-e255a96aca21" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NetCashProvidedByUsedInOperatingActivities_019feb9f-5f4e-7ecb-a0ac-456805ea47f9" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_NetCashProvidedByUsedInOperatingActivities"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NetIncomeLoss_019feb9f-5f4e-7b08-8729-0d6e942f181c" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_NetIncomeLoss"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInOperatingActivities_019feb9f-5f4e-7ecb-a0ac-456805ea47f9" xlink:to="loc_us-gaap_NetIncomeLoss_019feb9f-5f4e-7b08-8729-0d6e942f181c" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShareBasedCompensation_019feb9f-5f4e-7373-880e-abcc9366d414" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ShareBasedCompensation"/>
    <link:calculationArc order="2" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInOperatingActivities_019feb9f-5f4e-7ecb-a0ac-456805ea47f9" xlink:to="loc_us-gaap_ShareBasedCompensation_019feb9f-5f4e-7373-880e-abcc9366d414" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AdjustmentOfWarrantsGrantedForServices_019feb9f-5f4e-75ed-b314-3d45d34458d5" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_AdjustmentOfWarrantsGrantedForServices"/>
    <link:calculationArc order="3" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInOperatingActivities_019feb9f-5f4e-7ecb-a0ac-456805ea47f9" xlink:to="loc_us-gaap_AdjustmentOfWarrantsGrantedForServices_019feb9f-5f4e-75ed-b314-3d45d34458d5" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DepreciationAmortizationAndAccretionNet_019feb9f-5f4e-77f0-972e-3e10d980a3ab" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DepreciationAmortizationAndAccretionNet"/>
    <link:calculationArc order="4" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInOperatingActivities_019feb9f-5f4e-7ecb-a0ac-456805ea47f9" xlink:to="loc_us-gaap_DepreciationAmortizationAndAccretionNet_019feb9f-5f4e-77f0-972e-3e10d980a3ab" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PremiumReceivableCreditLossExpenseReversal_019feb9f-5f4e-7f17-8384-373e3530775a" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_PremiumReceivableCreditLossExpenseReversal"/>
    <link:calculationArc order="5" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInOperatingActivities_019feb9f-5f4e-7ecb-a0ac-456805ea47f9" xlink:to="loc_us-gaap_PremiumReceivableCreditLossExpenseReversal_019feb9f-5f4e-7f17-8384-373e3530775a" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_GainsLossesOnExtinguishmentOfDebt_019feb9f-5f4e-7903-9d68-849ecdf5f99a" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_GainsLossesOnExtinguishmentOfDebt"/>
    <link:calculationArc order="6" weight="-1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInOperatingActivities_019feb9f-5f4e-7ecb-a0ac-456805ea47f9" xlink:to="loc_us-gaap_GainsLossesOnExtinguishmentOfDebt_019feb9f-5f4e-7903-9d68-849ecdf5f99a" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_RealizedInvestmentGainsLosses_019feb9f-5f4e-7022-911a-c30b1fc1ef1f" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_RealizedInvestmentGainsLosses"/>
    <link:calculationArc order="7" weight="-1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInOperatingActivities_019feb9f-5f4e-7ecb-a0ac-456805ea47f9" xlink:to="loc_us-gaap_RealizedInvestmentGainsLosses_019feb9f-5f4e-7022-911a-c30b1fc1ef1f" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EquitySecuritiesFvNiGainLoss_019feb9f-5f4e-707c-b35f-4878272c8bb1" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_EquitySecuritiesFvNiGainLoss"/>
    <link:calculationArc order="8" weight="-1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInOperatingActivities_019feb9f-5f4e-7ecb-a0ac-456805ea47f9" xlink:to="loc_us-gaap_EquitySecuritiesFvNiGainLoss_019feb9f-5f4e-707c-b35f-4878272c8bb1" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncreaseDecreaseInPremiumsReceivable_019feb9f-5f4e-70c5-8052-f765a0074750" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_IncreaseDecreaseInPremiumsReceivable"/>
    <link:calculationArc order="9" weight="-1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInOperatingActivities_019feb9f-5f4e-7ecb-a0ac-456805ea47f9" xlink:to="loc_us-gaap_IncreaseDecreaseInPremiumsReceivable_019feb9f-5f4e-70c5-8052-f765a0074750" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_root_IncreaseDecreaseInReinsurancePremiumsReceivable_019feb9f-5f4e-7de4-8bbf-db870b70ce07" xlink:href="root-20260930.xsd#root_IncreaseDecreaseInReinsurancePremiumsReceivable"/>
    <link:calculationArc order="10" weight="-1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInOperatingActivities_019feb9f-5f4e-7ecb-a0ac-456805ea47f9" xlink:to="loc_root_IncreaseDecreaseInReinsurancePremiumsReceivable_019feb9f-5f4e-7de4-8bbf-db870b70ce07" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncreaseDecreaseInReinsuranceRecoverable_019feb9f-5f4e-7976-be2f-34517d7e60e7" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_IncreaseDecreaseInReinsuranceRecoverable"/>
    <link:calculationArc order="11" weight="-1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInOperatingActivities_019feb9f-5f4e-7ecb-a0ac-456805ea47f9" xlink:to="loc_us-gaap_IncreaseDecreaseInReinsuranceRecoverable_019feb9f-5f4e-7976-be2f-34517d7e60e7" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncreaseDecreaseInDeferredPolicyAcquisitionCosts_019feb9f-5f4e-73f3-96a3-1cd79229da62" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_IncreaseDecreaseInDeferredPolicyAcquisitionCosts"/>
    <link:calculationArc order="12" weight="-1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInOperatingActivities_019feb9f-5f4e-7ecb-a0ac-456805ea47f9" xlink:to="loc_us-gaap_IncreaseDecreaseInDeferredPolicyAcquisitionCosts_019feb9f-5f4e-73f3-96a3-1cd79229da62" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncreaseDecreaseInOtherOperatingAssets_019feb9f-5f4e-7c48-a282-f463158b0952" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_IncreaseDecreaseInOtherOperatingAssets"/>
    <link:calculationArc order="13" weight="-1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInOperatingActivities_019feb9f-5f4e-7ecb-a0ac-456805ea47f9" xlink:to="loc_us-gaap_IncreaseDecreaseInOtherOperatingAssets_019feb9f-5f4e-7c48-a282-f463158b0952" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncreaseDecreaseInLiabilityForClaimsAndClaimsAdjustmentExpenseReserve_019feb9f-5f4e-7041-baed-2ee1fb110042" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_IncreaseDecreaseInLiabilityForClaimsAndClaimsAdjustmentExpenseReserve"/>
    <link:calculationArc order="14" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInOperatingActivities_019feb9f-5f4e-7ecb-a0ac-456805ea47f9" xlink:to="loc_us-gaap_IncreaseDecreaseInLiabilityForClaimsAndClaimsAdjustmentExpenseReserve_019feb9f-5f4e-7041-baed-2ee1fb110042" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncreaseDecreaseInUnearnedPremiums_019feb9f-5f4e-7729-bbbb-37a73a97cf01" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_IncreaseDecreaseInUnearnedPremiums"/>
    <link:calculationArc order="15" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInOperatingActivities_019feb9f-5f4e-7ecb-a0ac-456805ea47f9" xlink:to="loc_us-gaap_IncreaseDecreaseInUnearnedPremiums_019feb9f-5f4e-7729-bbbb-37a73a97cf01" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_root_IncreaseDecreaseInPremiumsPayables_019feb9f-5f4e-79ff-b2a6-a0a24a77551f" xlink:href="root-20260930.xsd#root_IncreaseDecreaseInPremiumsPayables"/>
    <link:calculationArc order="16" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInOperatingActivities_019feb9f-5f4e-7ecb-a0ac-456805ea47f9" xlink:to="loc_root_IncreaseDecreaseInPremiumsPayables_019feb9f-5f4e-79ff-b2a6-a0a24a77551f" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncreaseDecreaseInAccountsPayableAndAccruedLiabilities_019feb9f-5f4e-7f18-9b45-47df78efc9cc" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_IncreaseDecreaseInAccountsPayableAndAccruedLiabilities"/>
    <link:calculationArc order="17" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInOperatingActivities_019feb9f-5f4e-7ecb-a0ac-456805ea47f9" xlink:to="loc_us-gaap_IncreaseDecreaseInAccountsPayableAndAccruedLiabilities_019feb9f-5f4e-7f18-9b45-47df78efc9cc" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncreaseDecreaseInOtherOperatingLiabilities_019feb9f-5f4e-7cd3-a6a1-dbb8434c1a01" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_IncreaseDecreaseInOtherOperatingLiabilities"/>
    <link:calculationArc order="18" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInOperatingActivities_019feb9f-5f4e-7ecb-a0ac-456805ea47f9" xlink:to="loc_us-gaap_IncreaseDecreaseInOtherOperatingLiabilities_019feb9f-5f4e-7cd3-a6a1-dbb8434c1a01" xlink:type="arc"/>
  </link:calculationLink>
  <link:roleRef roleURI="http://www.joinroot.com/role/BASISOFPRESENTATIONANDSUMMARYOFSIGNIFICANTACCOUNTINGPOLICIESScheduleofCashCashEquivalentsRestrictedCashandRestrictedCashEquivalentsDetails" xlink:type="simple" xlink:href="root-20260930.xsd#BASISOFPRESENTATIONANDSUMMARYOFSIGNIFICANTACCOUNTINGPOLICIESScheduleofCashCashEquivalentsRestrictedCashandRestrictedCashEquivalentsDetails"/>
  <link:calculationLink xlink:role="http://www.joinroot.com/role/BASISOFPRESENTATIONANDSUMMARYOFSIGNIFICANTACCOUNTINGPOLICIESScheduleofCashCashEquivalentsRestrictedCashandRestrictedCashEquivalentsDetails" xlink:type="extended">
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalents_019feb9f-5f4e-7012-81d3-f27d97c99381" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalents"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CashAndCashEquivalentsAtCarryingValue_019feb9f-5f4e-7171-bd21-e7722f4bacb2" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_CashAndCashEquivalentsAtCarryingValue"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalents_019feb9f-5f4e-7012-81d3-f27d97c99381" xlink:to="loc_us-gaap_CashAndCashEquivalentsAtCarryingValue_019feb9f-5f4e-7171-bd21-e7722f4bacb2" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_RestrictedCashAndCashEquivalents_019feb9f-5f4e-78fb-af7d-d75d6ddd749c" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_RestrictedCashAndCashEquivalents"/>
    <link:calculationArc order="2" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalents_019feb9f-5f4e-7012-81d3-f27d97c99381" xlink:to="loc_us-gaap_RestrictedCashAndCashEquivalents_019feb9f-5f4e-78fb-af7d-d75d6ddd749c" xlink:type="arc"/>
  </link:calculationLink>
  <link:roleRef roleURI="http://www.joinroot.com/role/INVESTMENTSScheduleofAmortizedCostandFairValueDetails" xlink:type="simple" xlink:href="root-20260930.xsd#INVESTMENTSScheduleofAmortizedCostandFairValueDetails"/>
  <link:calculationLink xlink:role="http://www.joinroot.com/role/INVESTMENTSScheduleofAmortizedCostandFairValueDetails" xlink:type="extended">
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtSecuritiesAvailableForSaleAmortizedCostExcludingAccruedInterestBeforeAllowanceForCreditLoss_019feb9f-5f4e-736f-9608-291bab560ca8" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DebtSecuritiesAvailableForSaleAmortizedCostExcludingAccruedInterestBeforeAllowanceForCreditLoss"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AvailableForSaleDebtSecuritiesAccumulatedGrossUnrealizedLossBeforeTax_019feb9f-5f4e-73ae-b471-5e34fed5e0dd" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_AvailableForSaleDebtSecuritiesAccumulatedGrossUnrealizedLossBeforeTax"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_DebtSecuritiesAvailableForSaleAmortizedCostExcludingAccruedInterestBeforeAllowanceForCreditLoss_019feb9f-5f4e-736f-9608-291bab560ca8" xlink:to="loc_us-gaap_AvailableForSaleDebtSecuritiesAccumulatedGrossUnrealizedLossBeforeTax_019feb9f-5f4e-73ae-b471-5e34fed5e0dd" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtSecuritiesAvailableForSaleExcludingAccruedInterest_019feb9f-5f4e-7573-bf43-b92fce12536a" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DebtSecuritiesAvailableForSaleExcludingAccruedInterest"/>
    <link:calculationArc order="2" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_DebtSecuritiesAvailableForSaleAmortizedCostExcludingAccruedInterestBeforeAllowanceForCreditLoss_019feb9f-5f4e-736f-9608-291bab560ca8" xlink:to="loc_us-gaap_DebtSecuritiesAvailableForSaleExcludingAccruedInterest_019feb9f-5f4e-7573-bf43-b92fce12536a" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AvailableForSaleDebtSecuritiesAccumulatedGrossUnrealizedGainBeforeTax_019feb9f-5f4e-7c70-902e-42c82b152032" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_AvailableForSaleDebtSecuritiesAccumulatedGrossUnrealizedGainBeforeTax"/>
    <link:calculationArc order="3" weight="-1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_DebtSecuritiesAvailableForSaleAmortizedCostExcludingAccruedInterestBeforeAllowanceForCreditLoss_019feb9f-5f4e-736f-9608-291bab560ca8" xlink:to="loc_us-gaap_AvailableForSaleDebtSecuritiesAccumulatedGrossUnrealizedGainBeforeTax_019feb9f-5f4e-7c70-902e-42c82b152032" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtSecuritiesAvailableForSaleAmortizedCostAllowanceForCreditLossExcludingAccruedInterest_019feb9f-5f4e-7e9e-99c2-8a60aaa579fb" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DebtSecuritiesAvailableForSaleAmortizedCostAllowanceForCreditLossExcludingAccruedInterest"/>
    <link:calculationArc order="4" weight="-1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_DebtSecuritiesAvailableForSaleAmortizedCostExcludingAccruedInterestBeforeAllowanceForCreditLoss_019feb9f-5f4e-736f-9608-291bab560ca8" xlink:to="loc_us-gaap_DebtSecuritiesAvailableForSaleAmortizedCostAllowanceForCreditLossExcludingAccruedInterest_019feb9f-5f4e-7e9e-99c2-8a60aaa579fb" xlink:type="arc"/>
  </link:calculationLink>
  <link:roleRef roleURI="http://www.joinroot.com/role/INVESTMENTSScheduleofUnrealizedLossesDetails" xlink:type="simple" xlink:href="root-20260930.xsd#INVESTMENTSScheduleofUnrealizedLossesDetails"/>
  <link:calculationLink xlink:role="http://www.joinroot.com/role/INVESTMENTSScheduleofUnrealizedLossesDetails" xlink:type="extended">
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtSecuritiesAvailableForSaleUnrealizedLossPosition_019feb9f-5f4e-7c71-8484-fdd3327da45f" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DebtSecuritiesAvailableForSaleUnrealizedLossPosition"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPosition12MonthsOrLonger_019feb9f-5f4e-74d5-9cf0-8ddbdd4aab19" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPosition12MonthsOrLonger"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_DebtSecuritiesAvailableForSaleUnrealizedLossPosition_019feb9f-5f4e-7c71-8484-fdd3327da45f" xlink:to="loc_us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPosition12MonthsOrLonger_019feb9f-5f4e-74d5-9cf0-8ddbdd4aab19" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPositionLessThan12Months_019feb9f-5f4e-747c-a124-4bfd97286b91" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPositionLessThan12Months"/>
    <link:calculationArc order="2" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_DebtSecuritiesAvailableForSaleUnrealizedLossPosition_019feb9f-5f4e-7c71-8484-fdd3327da45f" xlink:to="loc_us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPositionLessThan12Months_019feb9f-5f4e-747c-a124-4bfd97286b91" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtSecuritiesAvailableForSaleUnrealizedLossPositionAccumulatedLoss_019feb9f-5f4e-7311-a595-0d746b865a26" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DebtSecuritiesAvailableForSaleUnrealizedLossPositionAccumulatedLoss"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPositionLessThan12MonthsAccumulatedLoss_019feb9f-5f4e-7694-a79b-77fe7822998d" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPositionLessThan12MonthsAccumulatedLoss"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_DebtSecuritiesAvailableForSaleUnrealizedLossPositionAccumulatedLoss_019feb9f-5f4e-7311-a595-0d746b865a26" xlink:to="loc_us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPositionLessThan12MonthsAccumulatedLoss_019feb9f-5f4e-7694-a79b-77fe7822998d" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPosition12MonthsOrLongerAccumulatedLoss_019feb9f-5f4e-7ad8-88ba-0d808bbb39cd" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPosition12MonthsOrLongerAccumulatedLoss"/>
    <link:calculationArc order="2" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_DebtSecuritiesAvailableForSaleUnrealizedLossPositionAccumulatedLoss_019feb9f-5f4e-7311-a595-0d746b865a26" xlink:to="loc_us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPosition12MonthsOrLongerAccumulatedLoss_019feb9f-5f4e-7ad8-88ba-0d808bbb39cd" xlink:type="arc"/>
  </link:calculationLink>
  <link:roleRef roleURI="http://www.joinroot.com/role/INVESTMENTSScheduleofGrossandNetRealizedGainsandLossesDetails" xlink:type="simple" xlink:href="root-20260930.xsd#INVESTMENTSScheduleofGrossandNetRealizedGainsandLossesDetails"/>
  <link:calculationLink xlink:role="http://www.joinroot.com/role/INVESTMENTSScheduleofGrossandNetRealizedGainsandLossesDetails" xlink:type="extended">
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtSecuritiesAvailableForSaleRealizedGainLoss_019feb9f-5f4f-7fbb-aef1-72e932bc0a04" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DebtSecuritiesAvailableForSaleRealizedGainLoss"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtSecuritiesAvailableForSaleRealizedGain_019feb9f-5f4f-7138-b917-0d153e6205aa" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DebtSecuritiesAvailableForSaleRealizedGain"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_DebtSecuritiesAvailableForSaleRealizedGainLoss_019feb9f-5f4f-7fbb-aef1-72e932bc0a04" xlink:to="loc_us-gaap_DebtSecuritiesAvailableForSaleRealizedGain_019feb9f-5f4f-7138-b917-0d153e6205aa" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtSecuritiesAvailableForSaleRealizedLoss_019feb9f-5f4f-79d1-86a5-fe8f949ea4ae" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DebtSecuritiesAvailableForSaleRealizedLoss"/>
    <link:calculationArc order="2" weight="-1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_DebtSecuritiesAvailableForSaleRealizedGainLoss_019feb9f-5f4f-7fbb-aef1-72e932bc0a04" xlink:to="loc_us-gaap_DebtSecuritiesAvailableForSaleRealizedLoss_019feb9f-5f4f-79d1-86a5-fe8f949ea4ae" xlink:type="arc"/>
  </link:calculationLink>
  <link:roleRef roleURI="http://www.joinroot.com/role/INVESTMENTSScheduleofContractualMaturityDetails" xlink:type="simple" xlink:href="root-20260930.xsd#INVESTMENTSScheduleofContractualMaturityDetails"/>
  <link:calculationLink xlink:role="http://www.joinroot.com/role/INVESTMENTSScheduleofContractualMaturityDetails" xlink:type="extended">
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtSecuritiesAvailableForSaleExcludingAccruedInterest_019feb9f-5f4f-7aba-8c26-042ce7151f57" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DebtSecuritiesAvailableForSaleExcludingAccruedInterest"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterTenYearsFairValue_019feb9f-5f4f-7f26-a67c-3ac4b99b5417" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterTenYearsFairValue"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_DebtSecuritiesAvailableForSaleExcludingAccruedInterest_019feb9f-5f4f-7aba-8c26-042ce7151f57" xlink:to="loc_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterTenYearsFairValue_019feb9f-5f4f-7f26-a67c-3ac4b99b5417" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterFiveThroughTenYearsFairValue_019feb9f-5f4f-754a-8ac3-22e4ed6b47c5" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterFiveThroughTenYearsFairValue"/>
    <link:calculationArc order="2" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_DebtSecuritiesAvailableForSaleExcludingAccruedInterest_019feb9f-5f4f-7aba-8c26-042ce7151f57" xlink:to="loc_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterFiveThroughTenYearsFairValue_019feb9f-5f4f-754a-8ac3-22e4ed6b47c5" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesWithinOneYearFairValue_019feb9f-5f4f-7b97-96b2-33fb26063ef3" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_AvailableForSaleSecuritiesDebtMaturitiesWithinOneYearFairValue"/>
    <link:calculationArc order="3" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_DebtSecuritiesAvailableForSaleExcludingAccruedInterest_019feb9f-5f4f-7aba-8c26-042ce7151f57" xlink:to="loc_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesWithinOneYearFairValue_019feb9f-5f4f-7b97-96b2-33fb26063ef3" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterOneThroughFiveYearsFairValue_019feb9f-5f4f-725c-9ad7-4b5e3050da1b" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterOneThroughFiveYearsFairValue"/>
    <link:calculationArc order="4" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_DebtSecuritiesAvailableForSaleExcludingAccruedInterest_019feb9f-5f4f-7aba-8c26-042ce7151f57" xlink:to="loc_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterOneThroughFiveYearsFairValue_019feb9f-5f4f-725c-9ad7-4b5e3050da1b" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtSecuritiesAvailableForSaleAmortizedCostExcludingAccruedInterestBeforeAllowanceForCreditLoss_019feb9f-5f4f-7c36-9541-de990b32bae1" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DebtSecuritiesAvailableForSaleAmortizedCostExcludingAccruedInterestBeforeAllowanceForCreditLoss"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterOneThroughFiveYearsAmortizedCost_019feb9f-5f4f-788a-b611-72ab37fe1482" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterOneThroughFiveYearsAmortizedCost"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_DebtSecuritiesAvailableForSaleAmortizedCostExcludingAccruedInterestBeforeAllowanceForCreditLoss_019feb9f-5f4f-7c36-9541-de990b32bae1" xlink:to="loc_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterOneThroughFiveYearsAmortizedCost_019feb9f-5f4f-788a-b611-72ab37fe1482" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesWithinOneYearAmortizedCost_019feb9f-5f4f-7edd-9e33-f6bbba0d002d" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_AvailableForSaleSecuritiesDebtMaturitiesWithinOneYearAmortizedCost"/>
    <link:calculationArc order="2" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_DebtSecuritiesAvailableForSaleAmortizedCostExcludingAccruedInterestBeforeAllowanceForCreditLoss_019feb9f-5f4f-7c36-9541-de990b32bae1" xlink:to="loc_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesWithinOneYearAmortizedCost_019feb9f-5f4f-7edd-9e33-f6bbba0d002d" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterFiveThroughTenYearsAmortizedCost_019feb9f-5f4f-708a-852b-2933e18bbce5" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterFiveThroughTenYearsAmortizedCost"/>
    <link:calculationArc order="3" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_DebtSecuritiesAvailableForSaleAmortizedCostExcludingAccruedInterestBeforeAllowanceForCreditLoss_019feb9f-5f4f-7c36-9541-de990b32bae1" xlink:to="loc_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterFiveThroughTenYearsAmortizedCost_019feb9f-5f4f-708a-852b-2933e18bbce5" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterTenYearsAmortizedCost_019feb9f-5f4f-7f9b-be7c-465c6f3e4eee" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterTenYearsAmortizedCost"/>
    <link:calculationArc order="4" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_DebtSecuritiesAvailableForSaleAmortizedCostExcludingAccruedInterestBeforeAllowanceForCreditLoss_019feb9f-5f4f-7c36-9541-de990b32bae1" xlink:to="loc_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterTenYearsAmortizedCost_019feb9f-5f4f-7f9b-be7c-465c6f3e4eee" xlink:type="arc"/>
  </link:calculationLink>
  <link:roleRef roleURI="http://www.joinroot.com/role/INVESTMENTSScheduleofNetInvestmentIncomeDetails" xlink:type="simple" xlink:href="root-20260930.xsd#INVESTMENTSScheduleofNetInvestmentIncomeDetails"/>
  <link:calculationLink xlink:role="http://www.joinroot.com/role/INVESTMENTSScheduleofNetInvestmentIncomeDetails" xlink:type="extended">
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NetInvestmentIncome_019feb9f-5f4f-778b-8206-adc042814bed" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_NetInvestmentIncome"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_GrossInvestmentIncomeOperating_019feb9f-5f4f-797e-84d6-d5a99a2538e4" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_GrossInvestmentIncomeOperating"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_NetInvestmentIncome_019feb9f-5f4f-778b-8206-adc042814bed" xlink:to="loc_us-gaap_GrossInvestmentIncomeOperating_019feb9f-5f4f-797e-84d6-d5a99a2538e4" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_root_OtherInvestmentsImpairmentLoss_019feb9f-5f4f-78a5-bb2a-b69bfaee9e63" xlink:href="root-20260930.xsd#root_OtherInvestmentsImpairmentLoss"/>
    <link:calculationArc order="2" weight="-1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_NetInvestmentIncome_019feb9f-5f4f-778b-8206-adc042814bed" xlink:to="loc_root_OtherInvestmentsImpairmentLoss_019feb9f-5f4f-78a5-bb2a-b69bfaee9e63" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_InvestmentIncomeInvestmentExpense_019feb9f-5f4f-75b6-adb2-c088466a76a6" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_InvestmentIncomeInvestmentExpense"/>
    <link:calculationArc order="3" weight="-1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_NetInvestmentIncome_019feb9f-5f4f-778b-8206-adc042814bed" xlink:to="loc_us-gaap_InvestmentIncomeInvestmentExpense_019feb9f-5f4f-75b6-adb2-c088466a76a6" xlink:type="arc"/>
  </link:calculationLink>
  <link:roleRef roleURI="http://www.joinroot.com/role/FAIRVALUEOFFINANCIALINSTRUMENTSScheduleofFairValueofAssetsandLiabilitiesDetails" xlink:type="simple" xlink:href="root-20260930.xsd#FAIRVALUEOFFINANCIALINSTRUMENTSScheduleofFairValueofAssetsandLiabilitiesDetails"/>
  <link:calculationLink xlink:role="http://www.joinroot.com/role/FAIRVALUEOFFINANCIALINSTRUMENTSScheduleofFairValueofAssetsandLiabilitiesDetails" xlink:type="extended">
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AssetsFairValueDisclosure_019feb9f-5f4f-7bf8-9ae0-5d91d41712e7" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_AssetsFairValueDisclosure"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtSecuritiesAvailableForSaleExcludingAccruedInterest_019feb9f-5f4f-75fc-a500-09309b790168" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DebtSecuritiesAvailableForSaleExcludingAccruedInterest"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_AssetsFairValueDisclosure_019feb9f-5f4f-7bf8-9ae0-5d91d41712e7" xlink:to="loc_us-gaap_DebtSecuritiesAvailableForSaleExcludingAccruedInterest_019feb9f-5f4f-75fc-a500-09309b790168" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CashAndCashEquivalentsFairValueDisclosure_019feb9f-5f4f-7b39-afcf-598dd57cb5f1" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_CashAndCashEquivalentsFairValueDisclosure"/>
    <link:calculationArc order="2" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_AssetsFairValueDisclosure_019feb9f-5f4f-7bf8-9ae0-5d91d41712e7" xlink:to="loc_us-gaap_CashAndCashEquivalentsFairValueDisclosure_019feb9f-5f4f-7b39-afcf-598dd57cb5f1" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_root_RestrictedCashAndCashEquivalentsFairValueDisclosure_019feb9f-5f4f-76b7-ac06-f42b348e1fb8" xlink:href="root-20260930.xsd#root_RestrictedCashAndCashEquivalentsFairValueDisclosure"/>
    <link:calculationArc order="3" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_AssetsFairValueDisclosure_019feb9f-5f4f-7bf8-9ae0-5d91d41712e7" xlink:to="loc_root_RestrictedCashAndCashEquivalentsFairValueDisclosure_019feb9f-5f4f-76b7-ac06-f42b348e1fb8" xlink:type="arc"/>
  </link:calculationLink>
  <link:roleRef roleURI="http://www.joinroot.com/role/LOSSANDLOSSADJUSTMENTEXPENSERESERVESScheduleofReserveBalanceDetails" xlink:type="simple" xlink:href="root-20260930.xsd#LOSSANDLOSSADJUSTMENTEXPENSERESERVESScheduleofReserveBalanceDetails"/>
  <link:calculationLink xlink:role="http://www.joinroot.com/role/LOSSANDLOSSADJUSTMENTEXPENSERESERVESScheduleofReserveBalanceDetails" xlink:type="extended">
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaims1_019feb9f-5f4f-71ca-bc84-1df593917b1c" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaims1"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersPriorYearClaimsAndClaimsAdjustmentExpense_019feb9f-5f4f-706b-acc0-d6441982bd4c" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersPriorYearClaimsAndClaimsAdjustmentExpense"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaims1_019feb9f-5f4f-71ca-bc84-1df593917b1c" xlink:to="loc_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersPriorYearClaimsAndClaimsAdjustmentExpense_019feb9f-5f4f-706b-acc0-d6441982bd4c" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersCurrentYearClaimsAndClaimsAdjustmentExpense_019feb9f-5f4f-71fe-ad0c-b3e7338f3ba8" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersCurrentYearClaimsAndClaimsAdjustmentExpense"/>
    <link:calculationArc order="2" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaims1_019feb9f-5f4f-71ca-bc84-1df593917b1c" xlink:to="loc_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersCurrentYearClaimsAndClaimsAdjustmentExpense_019feb9f-5f4f-71fe-ad0c-b3e7338f3ba8" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PaymentsForLossesAndLossAdjustmentExpense_019feb9f-5f4f-707a-bb7b-a7658bbac0b6" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_PaymentsForLossesAndLossAdjustmentExpense"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidPriorYears1_019feb9f-5f4f-7f4a-8190-2fec5475ae49" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidPriorYears1"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_PaymentsForLossesAndLossAdjustmentExpense_019feb9f-5f4f-707a-bb7b-a7658bbac0b6" xlink:to="loc_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidPriorYears1_019feb9f-5f4f-7f4a-8190-2fec5475ae49" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidCurrentYear1_019feb9f-5f4f-7dc8-9cd2-cf0f0c7b18bb" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidCurrentYear1"/>
    <link:calculationArc order="2" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_PaymentsForLossesAndLossAdjustmentExpense_019feb9f-5f4f-707a-bb7b-a7658bbac0b6" xlink:to="loc_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidCurrentYear1_019feb9f-5f4f-7dc8-9cd2-cf0f0c7b18bb" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseNet_019feb9f-5f4f-7c7e-ab37-30521bbfbe48" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseNet"/>
    <link:loc xlink:type="locator" xlink:label="loc_root_LiabilityForClaimsAndClaimsAdjustmentExpenseGross_019feb9f-5f4f-70a8-b424-c095a6317e41" xlink:href="root-20260930.xsd#root_LiabilityForClaimsAndClaimsAdjustmentExpenseGross"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseNet_019feb9f-5f4f-7c7e-ab37-30521bbfbe48" xlink:to="loc_root_LiabilityForClaimsAndClaimsAdjustmentExpenseGross_019feb9f-5f4f-70a8-b424-c095a6317e41" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ReinsuranceRecoverableForUnpaidClaimsAndClaimsAdjustments_019feb9f-5f4f-7e6c-bf21-61e26ebc25a4" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ReinsuranceRecoverableForUnpaidClaimsAndClaimsAdjustments"/>
    <link:calculationArc order="2" weight="-1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseNet_019feb9f-5f4f-7c7e-ab37-30521bbfbe48" xlink:to="loc_us-gaap_ReinsuranceRecoverableForUnpaidClaimsAndClaimsAdjustments_019feb9f-5f4f-7e6c-bf21-61e26ebc25a4" xlink:type="arc"/>
  </link:calculationLink>
  <link:roleRef roleURI="http://www.joinroot.com/role/REINSURANCEDetails" xlink:type="simple" xlink:href="root-20260930.xsd#REINSURANCEDetails"/>
  <link:calculationLink xlink:role="http://www.joinroot.com/role/REINSURANCEDetails" xlink:type="extended">
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PremiumsWrittenNet_019feb9f-5f4f-77c1-a176-c966f330ef01" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_PremiumsWrittenNet"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CededPremiumsWritten_019feb9f-5f4f-7390-b0e3-3c440f01afde" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_CededPremiumsWritten"/>
    <link:calculationArc order="1" weight="-1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_PremiumsWrittenNet_019feb9f-5f4f-77c1-a176-c966f330ef01" xlink:to="loc_us-gaap_CededPremiumsWritten_019feb9f-5f4f-7390-b0e3-3c440f01afde" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AssumedPremiumsWritten_019feb9f-5f4f-729f-88d9-890cc064aa9a" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_AssumedPremiumsWritten"/>
    <link:calculationArc order="2" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_PremiumsWrittenNet_019feb9f-5f4f-77c1-a176-c966f330ef01" xlink:to="loc_us-gaap_AssumedPremiumsWritten_019feb9f-5f4f-729f-88d9-890cc064aa9a" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DirectPremiumsWritten_019feb9f-5f4f-7a8e-80d8-2af2ce454d66" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DirectPremiumsWritten"/>
    <link:calculationArc order="3" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_PremiumsWrittenNet_019feb9f-5f4f-77c1-a176-c966f330ef01" xlink:to="loc_us-gaap_DirectPremiumsWritten_019feb9f-5f4f-7a8e-80d8-2af2ce454d66" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaims1_019feb9f-5f4f-7e7b-ab85-5cbe99523ad3" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaims1"/>
    <link:loc xlink:type="locator" xlink:label="loc_root_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsAssumed_019feb9f-5f4f-7ea1-93ff-bbe61f357c0d" xlink:href="root-20260930.xsd#root_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsAssumed"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaims1_019feb9f-5f4f-7e7b-ab85-5cbe99523ad3" xlink:to="loc_root_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsAssumed_019feb9f-5f4f-7ea1-93ff-bbe61f357c0d" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_root_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsGross_019feb9f-5f4f-7214-a26a-41dd3b56a236" xlink:href="root-20260930.xsd#root_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsGross"/>
    <link:calculationArc order="2" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaims1_019feb9f-5f4f-7e7b-ab85-5cbe99523ad3" xlink:to="loc_root_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsGross_019feb9f-5f4f-7214-a26a-41dd3b56a236" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_root_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsCeded_019feb9f-5f4f-7bca-ac31-4675f1f81b9c" xlink:href="root-20260930.xsd#root_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsCeded"/>
    <link:calculationArc order="3" weight="-1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaims1_019feb9f-5f4f-7e7b-ab85-5cbe99523ad3" xlink:to="loc_root_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsCeded_019feb9f-5f4f-7bca-ac31-4675f1f81b9c" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PremiumsEarnedNet_019feb9f-5f4f-774f-8934-0bbfc20bbf54" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_PremiumsEarnedNet"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DirectPremiumsEarned_019feb9f-5f4f-73d4-959a-3ec63b8c3180" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DirectPremiumsEarned"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_PremiumsEarnedNet_019feb9f-5f4f-774f-8934-0bbfc20bbf54" xlink:to="loc_us-gaap_DirectPremiumsEarned_019feb9f-5f4f-73d4-959a-3ec63b8c3180" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AssumedPremiumsEarned_019feb9f-5f4f-7262-90d3-b27731800900" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_AssumedPremiumsEarned"/>
    <link:calculationArc order="2" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_PremiumsEarnedNet_019feb9f-5f4f-774f-8934-0bbfc20bbf54" xlink:to="loc_us-gaap_AssumedPremiumsEarned_019feb9f-5f4f-7262-90d3-b27731800900" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CededPremiumsEarned_019feb9f-5f4f-7ae2-ac0c-0620ecf4683b" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_CededPremiumsEarned"/>
    <link:calculationArc order="3" weight="-1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_PremiumsEarnedNet_019feb9f-5f4f-774f-8934-0bbfc20bbf54" xlink:to="loc_us-gaap_CededPremiumsEarned_019feb9f-5f4f-7ae2-ac0c-0620ecf4683b" xlink:type="arc"/>
  </link:calculationLink>
  <link:roleRef roleURI="http://www.joinroot.com/role/LONGTERMDEBTScheduleofLongTermDebtDetails" xlink:type="simple" xlink:href="root-20260930.xsd#LONGTERMDEBTScheduleofLongTermDebtDetails"/>
  <link:calculationLink xlink:role="http://www.joinroot.com/role/LONGTERMDEBTScheduleofLongTermDebtDetails" xlink:type="extended">
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LongTermDebt_019feb9f-6002-755b-8039-6c6f23a1a75a" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_LongTermDebt"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtInstrumentCarryingAmount_019feb9f-6002-7734-8af1-38b21851d080" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DebtInstrumentCarryingAmount"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_LongTermDebt_019feb9f-6002-755b-8039-6c6f23a1a75a" xlink:to="loc_us-gaap_DebtInstrumentCarryingAmount_019feb9f-6002-7734-8af1-38b21851d080" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_InterestPayableCurrentAndNoncurrent_019feb9f-6002-79cc-99db-20574121bb23" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_InterestPayableCurrentAndNoncurrent"/>
    <link:calculationArc order="2" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_LongTermDebt_019feb9f-6002-755b-8039-6c6f23a1a75a" xlink:to="loc_us-gaap_InterestPayableCurrentAndNoncurrent_019feb9f-6002-79cc-99db-20574121bb23" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtInstrumentUnamortizedDiscountPremiumAndDebtIssuanceCostsNet_019feb9f-6002-7089-9433-280abf7b9c09" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DebtInstrumentUnamortizedDiscountPremiumAndDebtIssuanceCostsNet"/>
    <link:calculationArc order="3" weight="-1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_LongTermDebt_019feb9f-6002-755b-8039-6c6f23a1a75a" xlink:to="loc_us-gaap_DebtInstrumentUnamortizedDiscountPremiumAndDebtIssuanceCostsNet_019feb9f-6002-7089-9433-280abf7b9c09" xlink:type="arc"/>
  </link:calculationLink>
  <link:roleRef roleURI="http://www.joinroot.com/role/LONGTERMDEBTScheduleofRequiredPrincipalPaymentsonLongTermDebtDetails" xlink:type="simple" xlink:href="root-20260930.xsd#LONGTERMDEBTScheduleofRequiredPrincipalPaymentsonLongTermDebtDetails"/>
  <link:calculationLink xlink:role="http://www.joinroot.com/role/LONGTERMDEBTScheduleofRequiredPrincipalPaymentsonLongTermDebtDetails" xlink:type="extended">
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtInstrumentCarryingAmount_019feb9f-6002-71dc-b6e3-45705ef033a2" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DebtInstrumentCarryingAmount"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LongTermDebtMaturitiesRepaymentsOfPrincipalRemainderOfFiscalYear_019feb9f-6002-7472-a37b-8815f40f7a4a" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_LongTermDebtMaturitiesRepaymentsOfPrincipalRemainderOfFiscalYear"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_DebtInstrumentCarryingAmount_019feb9f-6002-71dc-b6e3-45705ef033a2" xlink:to="loc_us-gaap_LongTermDebtMaturitiesRepaymentsOfPrincipalRemainderOfFiscalYear_019feb9f-6002-7472-a37b-8815f40f7a4a" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LongTermDebtMaturitiesRepaymentsOfPrincipalInNextTwelveMonths_019feb9f-6002-7430-929d-a67395280fed" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_LongTermDebtMaturitiesRepaymentsOfPrincipalInNextTwelveMonths"/>
    <link:calculationArc order="2" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_DebtInstrumentCarryingAmount_019feb9f-6002-71dc-b6e3-45705ef033a2" xlink:to="loc_us-gaap_LongTermDebtMaturitiesRepaymentsOfPrincipalInNextTwelveMonths_019feb9f-6002-7430-929d-a67395280fed" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LongTermDebtMaturitiesRepaymentsOfPrincipalInYearTwo_019feb9f-6002-7234-92ab-bfc83ef99adc" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_LongTermDebtMaturitiesRepaymentsOfPrincipalInYearTwo"/>
    <link:calculationArc order="3" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_DebtInstrumentCarryingAmount_019feb9f-6002-71dc-b6e3-45705ef033a2" xlink:to="loc_us-gaap_LongTermDebtMaturitiesRepaymentsOfPrincipalInYearTwo_019feb9f-6002-7234-92ab-bfc83ef99adc" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LongTermDebtMaturitiesRepaymentsOfPrincipalInYearThree_019feb9f-6002-730a-b350-ddc0a4cb3f6f" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_LongTermDebtMaturitiesRepaymentsOfPrincipalInYearThree"/>
    <link:calculationArc order="4" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_DebtInstrumentCarryingAmount_019feb9f-6002-71dc-b6e3-45705ef033a2" xlink:to="loc_us-gaap_LongTermDebtMaturitiesRepaymentsOfPrincipalInYearThree_019feb9f-6002-730a-b350-ddc0a4cb3f6f" xlink:type="arc"/>
  </link:calculationLink>
  <link:roleRef roleURI="http://www.joinroot.com/role/OTHERCOMPREHENSIVELOSSINCOMEANDACCUMULATEDOTHERCOMPREHENSIVELOSSINCOMEDetails" xlink:type="simple" xlink:href="root-20260930.xsd#OTHERCOMPREHENSIVELOSSINCOMEANDACCUMULATEDOTHERCOMPREHENSIVELOSSINCOMEDetails"/>
  <link:calculationLink xlink:role="http://www.joinroot.com/role/OTHERCOMPREHENSIVELOSSINCOMEANDACCUMULATEDOTHERCOMPREHENSIVELOSSINCOMEDetails" xlink:type="extended">
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OtherComprehensiveIncomeLossNetOfTaxPortionAttributableToParent_019feb9f-6002-7b60-b611-d543e94464be" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_OtherComprehensiveIncomeLossNetOfTaxPortionAttributableToParent"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OciBeforeReclassificationsBeforeTaxAttributableToParent_019feb9f-6002-7d7e-9fbd-4d7dc1ff0d74" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_OciBeforeReclassificationsBeforeTaxAttributableToParent"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_OtherComprehensiveIncomeLossNetOfTaxPortionAttributableToParent_019feb9f-6002-7b60-b611-d543e94464be" xlink:to="loc_us-gaap_OciBeforeReclassificationsBeforeTaxAttributableToParent_019feb9f-6002-7d7e-9fbd-4d7dc1ff0d74" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ReclassificationFromAociCurrentPeriodBeforeTaxAttributableToParent_019feb9f-6002-79b7-98eb-24b2f727e422" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ReclassificationFromAociCurrentPeriodBeforeTaxAttributableToParent"/>
    <link:calculationArc order="2" weight="-1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_OtherComprehensiveIncomeLossNetOfTaxPortionAttributableToParent_019feb9f-6002-7b60-b611-d543e94464be" xlink:to="loc_us-gaap_ReclassificationFromAociCurrentPeriodBeforeTaxAttributableToParent_019feb9f-6002-79b7-98eb-24b2f727e422" xlink:type="arc"/>
  </link:calculationLink>
  <link:roleRef roleURI="http://www.joinroot.com/role/EARNINGSLOSSPERSHAREScheduleofComputationofBasicandDilutedLossEarningsPerShareDetails" xlink:type="simple" xlink:href="root-20260930.xsd#EARNINGSLOSSPERSHAREScheduleofComputationofBasicandDilutedLossEarningsPerShareDetails"/>
  <link:calculationLink xlink:role="http://www.joinroot.com/role/EARNINGSLOSSPERSHAREScheduleofComputationofBasicandDilutedLossEarningsPerShareDetails" xlink:type="extended">
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_WeightedAverageNumberOfDilutedSharesOutstanding_019feb9f-6002-781b-adce-9e1d6a9027b5" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_WeightedAverageNumberOfDilutedSharesOutstanding"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncrementalCommonSharesAttributableToShareBasedPaymentArrangements_019feb9f-6002-706c-8c8b-292c924bf132" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_IncrementalCommonSharesAttributableToShareBasedPaymentArrangements"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_WeightedAverageNumberOfDilutedSharesOutstanding_019feb9f-6002-781b-adce-9e1d6a9027b5" xlink:to="loc_us-gaap_IncrementalCommonSharesAttributableToShareBasedPaymentArrangements_019feb9f-6002-706c-8c8b-292c924bf132" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncrementalCommonSharesAttributableToConversionOfPreferredStock_019feb9f-6002-7977-b90a-9db96395b893" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_IncrementalCommonSharesAttributableToConversionOfPreferredStock"/>
    <link:calculationArc order="2" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_WeightedAverageNumberOfDilutedSharesOutstanding_019feb9f-6002-781b-adce-9e1d6a9027b5" xlink:to="loc_us-gaap_IncrementalCommonSharesAttributableToConversionOfPreferredStock_019feb9f-6002-7977-b90a-9db96395b893" xlink:type="arc"/>
  </link:calculationLink>
</link:linkbase>
