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

<!--XBRL Document Created with the Workiva Platform-->
<!--Copyright 2026 Workiva-->
<!--r:019e4723-6009-752e-bb2c-82024beb825d,g:58f9e7b3-72a9-4a43-b1e0-ee1af3d771bd-->
<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.trupanion.com/role/ConsolidatedStatementofOperations" xlink:type="simple" xlink:href="trup-20260630.xsd#ConsolidatedStatementofOperations"/>
  <link:calculationLink xlink:role="http://www.trupanion.com/role/ConsolidatedStatementofOperations" xlink:type="extended">
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NetIncomeLossAvailableToCommonStockholdersBasic_019e4723-60dc-7eac-b8d9-494927d0cc54" 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_IncomeTaxExpenseBenefit_019e4723-60dc-7ce6-9900-af940acc579d" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_IncomeTaxExpenseBenefit"/>
    <link:calculationArc order="1" weight="-1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_NetIncomeLossAvailableToCommonStockholdersBasic_019e4723-60dc-7eac-b8d9-494927d0cc54" xlink:to="loc_us-gaap_IncomeTaxExpenseBenefit_019e4723-60dc-7ce6-9900-af940acc579d" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncomeLossFromContinuingOperationsBeforeIncomeTaxesExtraordinaryItemsNoncontrollingInterest_019e4723-60dc-7463-a0fb-f9df6c4cc006" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_IncomeLossFromContinuingOperationsBeforeIncomeTaxesExtraordinaryItemsNoncontrollingInterest"/>
    <link:calculationArc order="2" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_NetIncomeLossAvailableToCommonStockholdersBasic_019e4723-60dc-7eac-b8d9-494927d0cc54" xlink:to="loc_us-gaap_IncomeLossFromContinuingOperationsBeforeIncomeTaxesExtraordinaryItemsNoncontrollingInterest_019e4723-60dc-7463-a0fb-f9df6c4cc006" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CostOfRevenue_019e4723-60dc-7487-9400-8297d363d543" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_CostOfRevenue"/>
    <link:loc xlink:type="locator" xlink:label="loc_trup_ClaimsExpense_019e4723-60dc-7aaa-9348-a390f68b3f3c" xlink:href="trup-20260630.xsd#trup_ClaimsExpense"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_CostOfRevenue_019e4723-60dc-7487-9400-8297d363d543" xlink:to="loc_trup_ClaimsExpense_019e4723-60dc-7aaa-9348-a390f68b3f3c" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_trup_OtherCostofServicesSold_019e4723-60dc-77bc-84e5-aa6d8467b51b" xlink:href="trup-20260630.xsd#trup_OtherCostofServicesSold"/>
    <link:calculationArc order="2" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_CostOfRevenue_019e4723-60dc-7487-9400-8297d363d543" xlink:to="loc_trup_OtherCostofServicesSold_019e4723-60dc-77bc-84e5-aa6d8467b51b" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OperatingIncomeLoss_019e4723-60dc-747b-a64c-b3360e332a36" 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_OperatingExpenses_019e4723-60dc-7e24-a949-767776f7f9f4" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_OperatingExpenses"/>
    <link:calculationArc order="1" weight="-1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_OperatingIncomeLoss_019e4723-60dc-747b-a64c-b3360e332a36" xlink:to="loc_us-gaap_OperatingExpenses_019e4723-60dc-7e24-a949-767776f7f9f4" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_Revenues_019e4723-60dc-7997-93f4-51f723707c09" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_Revenues"/>
    <link:calculationArc order="2" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_OperatingIncomeLoss_019e4723-60dc-747b-a64c-b3360e332a36" xlink:to="loc_us-gaap_Revenues_019e4723-60dc-7997-93f4-51f723707c09" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CostOfRevenue_019e4723-60dc-77c1-ab2a-5086848378b2" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_CostOfRevenue"/>
    <link:calculationArc order="3" weight="-1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_OperatingIncomeLoss_019e4723-60dc-747b-a64c-b3360e332a36" xlink:to="loc_us-gaap_CostOfRevenue_019e4723-60dc-77c1-ab2a-5086848378b2" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncomeLossFromEquityMethodInvestments_019e4723-60dc-75db-81bb-9003cd2f9c0d" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_IncomeLossFromEquityMethodInvestments"/>
    <link:calculationArc order="4" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_OperatingIncomeLoss_019e4723-60dc-747b-a64c-b3360e332a36" xlink:to="loc_us-gaap_IncomeLossFromEquityMethodInvestments_019e4723-60dc-75db-81bb-9003cd2f9c0d" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncomeLossFromContinuingOperationsBeforeIncomeTaxesExtraordinaryItemsNoncontrollingInterest_019e4723-60dc-7e0d-b0d5-92cc98eec763" 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_019e4723-60dc-74a0-b9e8-05de0b310216" 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_019e4723-60dc-7e0d-b0d5-92cc98eec763" xlink:to="loc_us-gaap_OperatingIncomeLoss_019e4723-60dc-74a0-b9e8-05de0b310216" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_InterestExpense_019e4723-60dc-7461-8484-e64bf0d90534" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_InterestExpense"/>
    <link:calculationArc order="2" weight="-1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_IncomeLossFromContinuingOperationsBeforeIncomeTaxesExtraordinaryItemsNoncontrollingInterest_019e4723-60dc-7e0d-b0d5-92cc98eec763" xlink:to="loc_us-gaap_InterestExpense_019e4723-60dc-7461-8484-e64bf0d90534" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OtherNonoperatingIncomeExpense_019e4723-60dc-76a5-ae49-b9c8d72749e0" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_OtherNonoperatingIncomeExpense"/>
    <link:calculationArc order="3" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_IncomeLossFromContinuingOperationsBeforeIncomeTaxesExtraordinaryItemsNoncontrollingInterest_019e4723-60dc-7e0d-b0d5-92cc98eec763" xlink:to="loc_us-gaap_OtherNonoperatingIncomeExpense_019e4723-60dc-76a5-ae49-b9c8d72749e0" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OperatingExpenses_019e4723-60dc-7d16-a0ee-be5cc34fb88f" 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_us-gaap_SellingAndMarketingExpense_019e4723-60dc-7318-b15b-4f0e886674a1" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_SellingAndMarketingExpense"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_OperatingExpenses_019e4723-60dc-7d16-a0ee-be5cc34fb88f" xlink:to="loc_us-gaap_SellingAndMarketingExpense_019e4723-60dc-7318-b15b-4f0e886674a1" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DepreciationDepletionAndAmortization_019e4723-60dc-7308-bd0b-6a506cbea7ba" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DepreciationDepletionAndAmortization"/>
    <link:calculationArc order="2" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_OperatingExpenses_019e4723-60dc-7d16-a0ee-be5cc34fb88f" xlink:to="loc_us-gaap_DepreciationDepletionAndAmortization_019e4723-60dc-7308-bd0b-6a506cbea7ba" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_GeneralAndAdministrativeExpense_019e4723-60dc-7ce1-bb2a-4c3f6162dc18" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_GeneralAndAdministrativeExpense"/>
    <link:calculationArc order="3" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_OperatingExpenses_019e4723-60dc-7d16-a0ee-be5cc34fb88f" xlink:to="loc_us-gaap_GeneralAndAdministrativeExpense_019e4723-60dc-7ce1-bb2a-4c3f6162dc18" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_trup_TechnologyandDevelopmentExpense_019e4723-60dc-7397-becf-428ed8e06c49" xlink:href="trup-20260630.xsd#trup_TechnologyandDevelopmentExpense"/>
    <link:calculationArc order="4" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_OperatingExpenses_019e4723-60dc-7d16-a0ee-be5cc34fb88f" xlink:to="loc_trup_TechnologyandDevelopmentExpense_019e4723-60dc-7397-becf-428ed8e06c49" xlink:type="arc"/>
  </link:calculationLink>
  <link:roleRef roleURI="http://www.trupanion.com/role/ConsolidatedStatementofComprehensiveIncomeStatement" xlink:type="simple" xlink:href="trup-20260630.xsd#ConsolidatedStatementofComprehensiveIncomeStatement"/>
  <link:calculationLink xlink:role="http://www.trupanion.com/role/ConsolidatedStatementofComprehensiveIncomeStatement" xlink:type="extended">
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OtherComprehensiveIncomeLossNetOfTax_019e4723-60dc-73fb-a509-3341d3e16bca" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_OtherComprehensiveIncomeLossNetOfTax"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OtherComprehensiveIncomeLossForeignCurrencyTransactionAndTranslationAdjustmentNetOfTax_019e4723-60dc-7d9a-a387-54cf0d097c93" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_OtherComprehensiveIncomeLossForeignCurrencyTransactionAndTranslationAdjustmentNetOfTax"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_OtherComprehensiveIncomeLossNetOfTax_019e4723-60dc-73fb-a509-3341d3e16bca" xlink:to="loc_us-gaap_OtherComprehensiveIncomeLossForeignCurrencyTransactionAndTranslationAdjustmentNetOfTax_019e4723-60dc-7d9a-a387-54cf0d097c93" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OtherComprehensiveIncomeUnrealizedHoldingGainLossOnSecuritiesArisingDuringPeriodNetOfTax_019e4723-60dc-7d2e-aabc-9c06debeafdc" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_OtherComprehensiveIncomeUnrealizedHoldingGainLossOnSecuritiesArisingDuringPeriodNetOfTax"/>
    <link:calculationArc order="2" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_OtherComprehensiveIncomeLossNetOfTax_019e4723-60dc-73fb-a509-3341d3e16bca" xlink:to="loc_us-gaap_OtherComprehensiveIncomeUnrealizedHoldingGainLossOnSecuritiesArisingDuringPeriodNetOfTax_019e4723-60dc-7d2e-aabc-9c06debeafdc" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ComprehensiveIncomeNetOfTax_019e4723-60dc-701f-979a-65ca4cf3ad87" 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_OtherComprehensiveIncomeLossNetOfTax_019e4723-60dc-7819-88ea-177ec349fada" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_OtherComprehensiveIncomeLossNetOfTax"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_ComprehensiveIncomeNetOfTax_019e4723-60dc-701f-979a-65ca4cf3ad87" xlink:to="loc_us-gaap_OtherComprehensiveIncomeLossNetOfTax_019e4723-60dc-7819-88ea-177ec349fada" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NetIncomeLossAvailableToCommonStockholdersBasic_019e4723-60dc-7522-9780-e8d6c00323c5" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_NetIncomeLossAvailableToCommonStockholdersBasic"/>
    <link:calculationArc order="2" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_ComprehensiveIncomeNetOfTax_019e4723-60dc-701f-979a-65ca4cf3ad87" xlink:to="loc_us-gaap_NetIncomeLossAvailableToCommonStockholdersBasic_019e4723-60dc-7522-9780-e8d6c00323c5" xlink:type="arc"/>
  </link:calculationLink>
  <link:roleRef roleURI="http://www.trupanion.com/role/ConsolidatedBalanceSheet" xlink:type="simple" xlink:href="trup-20260630.xsd#ConsolidatedBalanceSheet"/>
  <link:calculationLink xlink:role="http://www.trupanion.com/role/ConsolidatedBalanceSheet" xlink:type="extended">
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LiabilitiesAndStockholdersEquity_019e4723-60dc-7b9a-a92e-d7f4b5853dd0" 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_019e4723-60dc-75af-b9be-f1cba49e54ef" 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_019e4723-60dc-7b9a-a92e-d7f4b5853dd0" xlink:to="loc_us-gaap_Liabilities_019e4723-60dc-75af-b9be-f1cba49e54ef" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_StockholdersEquity_019e4723-60dc-7c36-9c3e-140073d17d91" 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_019e4723-60dc-7b9a-a92e-d7f4b5853dd0" xlink:to="loc_us-gaap_StockholdersEquity_019e4723-60dc-7c36-9c3e-140073d17d91" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_Liabilities_019e4723-60dc-737e-a07e-9b2bb766a7d4" 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_us-gaap_DeferredIncomeTaxLiabilitiesNet_019e4723-60dc-7549-ba0e-0af86f6e0c8c" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DeferredIncomeTaxLiabilitiesNet"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_Liabilities_019e4723-60dc-737e-a07e-9b2bb766a7d4" xlink:to="loc_us-gaap_DeferredIncomeTaxLiabilitiesNet_019e4723-60dc-7549-ba0e-0af86f6e0c8c" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LongTermDebtNoncurrent_019e4723-60dc-7027-beaa-20db7a855479" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_LongTermDebtNoncurrent"/>
    <link:calculationArc order="2" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_Liabilities_019e4723-60dc-737e-a07e-9b2bb766a7d4" xlink:to="loc_us-gaap_LongTermDebtNoncurrent_019e4723-60dc-7027-beaa-20db7a855479" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OtherLiabilitiesNoncurrent_019e4723-60dc-71b8-9797-4aa7241bc813" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_OtherLiabilitiesNoncurrent"/>
    <link:calculationArc order="3" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_Liabilities_019e4723-60dc-737e-a07e-9b2bb766a7d4" xlink:to="loc_us-gaap_OtherLiabilitiesNoncurrent_019e4723-60dc-71b8-9797-4aa7241bc813" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LiabilitiesCurrent_019e4723-60dc-728e-a1f6-2ea5b6cabfe6" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_LiabilitiesCurrent"/>
    <link:calculationArc order="4" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_Liabilities_019e4723-60dc-737e-a07e-9b2bb766a7d4" xlink:to="loc_us-gaap_LiabilitiesCurrent_019e4723-60dc-728e-a1f6-2ea5b6cabfe6" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_StockholdersEquity_019e4723-60dc-7ad3-aca9-1977e5d22b7e" 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_CommonStockValueOutstanding_019e4723-60dc-7b6a-b8a3-03babf72d79c" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_CommonStockValueOutstanding"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_StockholdersEquity_019e4723-60dc-7ad3-aca9-1977e5d22b7e" xlink:to="loc_us-gaap_CommonStockValueOutstanding_019e4723-60dc-7b6a-b8a3-03babf72d79c" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PreferredStockValueOutstanding_019e4723-60dc-7ad0-b0c7-16f0729bd2e9" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_PreferredStockValueOutstanding"/>
    <link:calculationArc order="2" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_StockholdersEquity_019e4723-60dc-7ad3-aca9-1977e5d22b7e" xlink:to="loc_us-gaap_PreferredStockValueOutstanding_019e4723-60dc-7ad0-b0c7-16f0729bd2e9" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AdditionalPaidInCapital_019e4723-60dc-7f11-9c13-1dc32e627a34" 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_019e4723-60dc-7ad3-aca9-1977e5d22b7e" xlink:to="loc_us-gaap_AdditionalPaidInCapital_019e4723-60dc-7f11-9c13-1dc32e627a34" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AccumulatedOtherComprehensiveIncomeLossNetOfTax_019e4723-60dc-743e-a154-f2a7bc3eafe0" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_AccumulatedOtherComprehensiveIncomeLossNetOfTax"/>
    <link:calculationArc order="4" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_StockholdersEquity_019e4723-60dc-7ad3-aca9-1977e5d22b7e" xlink:to="loc_us-gaap_AccumulatedOtherComprehensiveIncomeLossNetOfTax_019e4723-60dc-743e-a154-f2a7bc3eafe0" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_RetainedEarningsAccumulatedDeficit_019e4723-60dc-7926-8497-c3cb707c8bdc" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_RetainedEarningsAccumulatedDeficit"/>
    <link:calculationArc order="5" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_StockholdersEquity_019e4723-60dc-7ad3-aca9-1977e5d22b7e" xlink:to="loc_us-gaap_RetainedEarningsAccumulatedDeficit_019e4723-60dc-7926-8497-c3cb707c8bdc" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_TreasuryStockValue_019e4723-60dc-7583-85f1-5ad2d0a8e13b" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_TreasuryStockValue"/>
    <link:calculationArc order="6" weight="-1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_StockholdersEquity_019e4723-60dc-7ad3-aca9-1977e5d22b7e" xlink:to="loc_us-gaap_TreasuryStockValue_019e4723-60dc-7583-85f1-5ad2d0a8e13b" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_Assets_019e4723-60dc-7ef2-906a-082074d8e3a7" 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_PropertyPlantAndEquipmentNet_019e4723-60dc-7dd9-987b-49c3d30528e8" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_PropertyPlantAndEquipmentNet"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_Assets_019e4723-60dc-7ef2-906a-082074d8e3a7" xlink:to="loc_us-gaap_PropertyPlantAndEquipmentNet_019e4723-60dc-7dd9-987b-49c3d30528e8" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_Goodwill_019e4723-60dc-7ba4-a6c0-2260f54bb7f2" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_Goodwill"/>
    <link:calculationArc order="2" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_Assets_019e4723-60dc-7ef2-906a-082074d8e3a7" xlink:to="loc_us-gaap_Goodwill_019e4723-60dc-7ba4-a6c0-2260f54bb7f2" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IntangibleAssetsNetExcludingGoodwill_019e4723-60dc-7be6-9e44-478c85a76137" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_IntangibleAssetsNetExcludingGoodwill"/>
    <link:calculationArc order="3" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_Assets_019e4723-60dc-7ef2-906a-082074d8e3a7" xlink:to="loc_us-gaap_IntangibleAssetsNetExcludingGoodwill_019e4723-60dc-7be6-9e44-478c85a76137" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_MarketableSecuritiesNoncurrent_019e4723-60dc-7a60-8a30-c7a18955033c" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_MarketableSecuritiesNoncurrent"/>
    <link:calculationArc order="4" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_Assets_019e4723-60dc-7ef2-906a-082074d8e3a7" xlink:to="loc_us-gaap_MarketableSecuritiesNoncurrent_019e4723-60dc-7a60-8a30-c7a18955033c" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AssetsCurrent_019e4723-60dc-71da-af41-994a90f63330" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_AssetsCurrent"/>
    <link:calculationArc order="5" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_Assets_019e4723-60dc-7ef2-906a-082074d8e3a7" xlink:to="loc_us-gaap_AssetsCurrent_019e4723-60dc-71da-af41-994a90f63330" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OtherAssetsNoncurrent_019e4723-60dc-7926-b100-36bc43ea5f05" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_OtherAssetsNoncurrent"/>
    <link:calculationArc order="6" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_Assets_019e4723-60dc-7ef2-906a-082074d8e3a7" xlink:to="loc_us-gaap_OtherAssetsNoncurrent_019e4723-60dc-7926-b100-36bc43ea5f05" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_RestrictedCashAndCashEquivalents_019e4723-60dc-7f12-b93a-9497713b918a" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_RestrictedCashAndCashEquivalents"/>
    <link:calculationArc order="7" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_Assets_019e4723-60dc-7ef2-906a-082074d8e3a7" xlink:to="loc_us-gaap_RestrictedCashAndCashEquivalents_019e4723-60dc-7f12-b93a-9497713b918a" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LiabilitiesCurrent_019e4723-60dc-7ae9-b6cc-594c78c414db" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_LiabilitiesCurrent"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AccruedLiabilitiesCurrent_019e4723-60dc-7b0b-b01a-c0c1aa46c377" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_AccruedLiabilitiesCurrent"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_LiabilitiesCurrent_019e4723-60dc-7ae9-b6cc-594c78c414db" xlink:to="loc_us-gaap_AccruedLiabilitiesCurrent_019e4723-60dc-7b0b-b01a-c0c1aa46c377" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LiabilityForClaimsAndClaimsAdjustmentExpense_019e4723-60dc-7530-bbb9-921dd4c86f06" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_LiabilityForClaimsAndClaimsAdjustmentExpense"/>
    <link:calculationArc order="2" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_LiabilitiesCurrent_019e4723-60dc-7ae9-b6cc-594c78c414db" xlink:to="loc_us-gaap_LiabilityForClaimsAndClaimsAdjustmentExpense_019e4723-60dc-7530-bbb9-921dd4c86f06" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DeferredRevenueCurrent_019e4723-60dc-78ba-9ce9-6ea808a7bf03" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DeferredRevenueCurrent"/>
    <link:calculationArc order="3" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_LiabilitiesCurrent_019e4723-60dc-7ae9-b6cc-594c78c414db" xlink:to="loc_us-gaap_DeferredRevenueCurrent_019e4723-60dc-78ba-9ce9-6ea808a7bf03" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AccountsPayableCurrent_019e4723-60dc-7f27-b5b7-29ffe61fc1af" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_AccountsPayableCurrent"/>
    <link:calculationArc order="4" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_LiabilitiesCurrent_019e4723-60dc-7ae9-b6cc-594c78c414db" xlink:to="loc_us-gaap_AccountsPayableCurrent_019e4723-60dc-7f27-b5b7-29ffe61fc1af" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LongTermDebtCurrent_019e4723-60dc-7966-ae20-38b234816f25" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_LongTermDebtCurrent"/>
    <link:calculationArc order="5" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_LiabilitiesCurrent_019e4723-60dc-7ae9-b6cc-594c78c414db" xlink:to="loc_us-gaap_LongTermDebtCurrent_019e4723-60dc-7966-ae20-38b234816f25" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AssetsCurrent_019e4723-60dc-7654-96a6-084e6d770f85" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_AssetsCurrent"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CashAndCashEquivalentsAtCarryingValue_019e4723-60dc-7319-a0af-adb12043f6f4" 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_AssetsCurrent_019e4723-60dc-7654-96a6-084e6d770f85" xlink:to="loc_us-gaap_CashAndCashEquivalentsAtCarryingValue_019e4723-60dc-7319-a0af-adb12043f6f4" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShortTermInvestments_019e4723-60dc-7ebf-8721-b593b86db75b" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ShortTermInvestments"/>
    <link:calculationArc order="2" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_AssetsCurrent_019e4723-60dc-7654-96a6-084e6d770f85" xlink:to="loc_us-gaap_ShortTermInvestments_019e4723-60dc-7ebf-8721-b593b86db75b" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AccountsAndOtherReceivablesNetCurrent_019e4723-60dc-79e3-a6fd-c5647fdab354" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_AccountsAndOtherReceivablesNetCurrent"/>
    <link:calculationArc order="3" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_AssetsCurrent_019e4723-60dc-7654-96a6-084e6d770f85" xlink:to="loc_us-gaap_AccountsAndOtherReceivablesNetCurrent_019e4723-60dc-79e3-a6fd-c5647fdab354" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PrepaidExpenseAndOtherAssets_019e4723-60dc-765e-980b-ce8bdf5d8d2c" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_PrepaidExpenseAndOtherAssets"/>
    <link:calculationArc order="4" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_AssetsCurrent_019e4723-60dc-7654-96a6-084e6d770f85" xlink:to="loc_us-gaap_PrepaidExpenseAndOtherAssets_019e4723-60dc-765e-980b-ce8bdf5d8d2c" xlink:type="arc"/>
  </link:calculationLink>
  <link:roleRef roleURI="http://www.trupanion.com/role/ConsolidatedStatementofCashFlows" xlink:type="simple" xlink:href="trup-20260630.xsd#ConsolidatedStatementofCashFlows"/>
  <link:calculationLink xlink:role="http://www.trupanion.com/role/ConsolidatedStatementofCashFlows" xlink:type="extended">
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NetCashProvidedByUsedInInvestingActivities_019e4723-60dc-7f28-9b65-08f7dd333c7f" 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_PaymentsForProceedsFromOtherInvestingActivities_019e4723-60dc-7844-9ce6-0d6d1815e3f2" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_PaymentsForProceedsFromOtherInvestingActivities"/>
    <link:calculationArc order="1" weight="-1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInInvestingActivities_019e4723-60dc-7f28-9b65-08f7dd333c7f" xlink:to="loc_us-gaap_PaymentsForProceedsFromOtherInvestingActivities_019e4723-60dc-7844-9ce6-0d6d1815e3f2" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PaymentsToAcquirePropertyPlantAndEquipment_019e4723-60dc-7c1f-9227-d38ca4b6818b" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_PaymentsToAcquirePropertyPlantAndEquipment"/>
    <link:calculationArc order="2" weight="-1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInInvestingActivities_019e4723-60dc-7f28-9b65-08f7dd333c7f" xlink:to="loc_us-gaap_PaymentsToAcquirePropertyPlantAndEquipment_019e4723-60dc-7c1f-9227-d38ca4b6818b" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ProceedsFromSaleAndMaturityOfHeldToMaturitySecurities_019e4723-60dc-7029-aea3-62f58630a437" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ProceedsFromSaleAndMaturityOfHeldToMaturitySecurities"/>
    <link:calculationArc order="3" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInInvestingActivities_019e4723-60dc-7f28-9b65-08f7dd333c7f" xlink:to="loc_us-gaap_ProceedsFromSaleAndMaturityOfHeldToMaturitySecurities_019e4723-60dc-7029-aea3-62f58630a437" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PaymentsToAcquireHeldToMaturitySecurities_019e4723-60dc-76a8-b705-f1a098a41ff3" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_PaymentsToAcquireHeldToMaturitySecurities"/>
    <link:calculationArc order="4" weight="-1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInInvestingActivities_019e4723-60dc-7f28-9b65-08f7dd333c7f" xlink:to="loc_us-gaap_PaymentsToAcquireHeldToMaturitySecurities_019e4723-60dc-76a8-b705-f1a098a41ff3" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NetCashProvidedByUsedInOperatingActivities_019e4723-60dc-78d0-9391-2db5d2980ff8" 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_NetIncomeLossAvailableToCommonStockholdersBasic_019e4723-60dc-74f0-9307-4bb5ab32eabb" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_NetIncomeLossAvailableToCommonStockholdersBasic"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInOperatingActivities_019e4723-60dc-78d0-9391-2db5d2980ff8" xlink:to="loc_us-gaap_NetIncomeLossAvailableToCommonStockholdersBasic_019e4723-60dc-74f0-9307-4bb5ab32eabb" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DepreciationDepletionAndAmortization_019e4723-60dc-78c0-9d68-1e6519580348" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DepreciationDepletionAndAmortization"/>
    <link:calculationArc order="2" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInOperatingActivities_019e4723-60dc-78d0-9391-2db5d2980ff8" xlink:to="loc_us-gaap_DepreciationDepletionAndAmortization_019e4723-60dc-78c0-9d68-1e6519580348" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShareBasedCompensation_019e4723-60dc-7966-b825-6594fa95ccc8" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ShareBasedCompensation"/>
    <link:calculationArc order="3" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInOperatingActivities_019e4723-60dc-78d0-9391-2db5d2980ff8" xlink:to="loc_us-gaap_ShareBasedCompensation_019e4723-60dc-7966-b825-6594fa95ccc8" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NonmonetaryTransactionGainLossRecognizedOnTransfer_019e4723-60dc-7092-a38c-df34aefb7df5" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_NonmonetaryTransactionGainLossRecognizedOnTransfer"/>
    <link:calculationArc order="4" weight="-1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInOperatingActivities_019e4723-60dc-78d0-9391-2db5d2980ff8" xlink:to="loc_us-gaap_NonmonetaryTransactionGainLossRecognizedOnTransfer_019e4723-60dc-7092-a38c-df34aefb7df5" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OtherOperatingIncomeExpenseNet_019e4723-60dc-7408-adfd-45af15c44b6d" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_OtherOperatingIncomeExpenseNet"/>
    <link:calculationArc order="5" weight="-1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInOperatingActivities_019e4723-60dc-78d0-9391-2db5d2980ff8" xlink:to="loc_us-gaap_OtherOperatingIncomeExpenseNet_019e4723-60dc-7408-adfd-45af15c44b6d" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncreaseDecreaseInAccountsReceivable_019e4723-60dc-7113-91a8-0d94874cd67d" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_IncreaseDecreaseInAccountsReceivable"/>
    <link:calculationArc order="6" weight="-1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInOperatingActivities_019e4723-60dc-78d0-9391-2db5d2980ff8" xlink:to="loc_us-gaap_IncreaseDecreaseInAccountsReceivable_019e4723-60dc-7113-91a8-0d94874cd67d" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncreaseDecreaseInPrepaidDeferredExpenseAndOtherAssets_019e4723-60dc-707d-b621-55cdf1127bc7" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_IncreaseDecreaseInPrepaidDeferredExpenseAndOtherAssets"/>
    <link:calculationArc order="7" weight="-1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInOperatingActivities_019e4723-60dc-78d0-9391-2db5d2980ff8" xlink:to="loc_us-gaap_IncreaseDecreaseInPrepaidDeferredExpenseAndOtherAssets_019e4723-60dc-707d-b621-55cdf1127bc7" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncreaseDecreaseInAccountsPayableAndAccruedLiabilities_019e4723-60dc-733c-8fa6-0526a57b552d" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_IncreaseDecreaseInAccountsPayableAndAccruedLiabilities"/>
    <link:calculationArc order="8" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInOperatingActivities_019e4723-60dc-78d0-9391-2db5d2980ff8" xlink:to="loc_us-gaap_IncreaseDecreaseInAccountsPayableAndAccruedLiabilities_019e4723-60dc-733c-8fa6-0526a57b552d" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_trup_IncreaseDecreaseinClaimsReserveandLossAdjustment_019e4723-60dc-7d3e-a9e9-9335119d353a" xlink:href="trup-20260630.xsd#trup_IncreaseDecreaseinClaimsReserveandLossAdjustment"/>
    <link:calculationArc order="9" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInOperatingActivities_019e4723-60dc-78d0-9391-2db5d2980ff8" xlink:to="loc_trup_IncreaseDecreaseinClaimsReserveandLossAdjustment_019e4723-60dc-7d3e-a9e9-9335119d353a" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncreaseDecreaseInUnearnedPremiums_019e4723-60dc-7f08-99a7-5c7b378f6dc6" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_IncreaseDecreaseInUnearnedPremiums"/>
    <link:calculationArc order="10" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInOperatingActivities_019e4723-60dc-78d0-9391-2db5d2980ff8" xlink:to="loc_us-gaap_IncreaseDecreaseInUnearnedPremiums_019e4723-60dc-7f08-99a7-5c7b378f6dc6" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NetCashProvidedByUsedInFinancingActivities_019e4723-60dc-7f48-b17b-6faaecce6736" 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_PaymentsRelatedToTaxWithholdingForShareBasedCompensation_019e4723-60dc-7796-b8af-f5479f375b69" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_PaymentsRelatedToTaxWithholdingForShareBasedCompensation"/>
    <link:calculationArc order="1" weight="-1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInFinancingActivities_019e4723-60dc-7f48-b17b-6faaecce6736" xlink:to="loc_us-gaap_PaymentsRelatedToTaxWithholdingForShareBasedCompensation_019e4723-60dc-7796-b8af-f5479f375b69" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_RepaymentsOfDebt_019e4723-60dc-7d0d-a321-eb18c81fa731" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_RepaymentsOfDebt"/>
    <link:calculationArc order="2" weight="-1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInFinancingActivities_019e4723-60dc-7f48-b17b-6faaecce6736" xlink:to="loc_us-gaap_RepaymentsOfDebt_019e4723-60dc-7d0d-a321-eb18c81fa731" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ProceedsFromStockOptionsExercised_019e4723-60dc-7f2e-ab04-7fef4cb2be78" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ProceedsFromStockOptionsExercised"/>
    <link:calculationArc order="3" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInFinancingActivities_019e4723-60dc-7f48-b17b-6faaecce6736" xlink:to="loc_us-gaap_ProceedsFromStockOptionsExercised_019e4723-60dc-7f2e-ab04-7fef4cb2be78" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ProceedsFromPaymentsForOtherFinancingActivities_019e4723-60dc-7207-85f9-1ce869cca9b1" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ProceedsFromPaymentsForOtherFinancingActivities"/>
    <link:calculationArc order="4" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInFinancingActivities_019e4723-60dc-7f48-b17b-6faaecce6736" xlink:to="loc_us-gaap_ProceedsFromPaymentsForOtherFinancingActivities_019e4723-60dc-7207-85f9-1ce869cca9b1" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalentsPeriodIncreaseDecreaseIncludingExchangeRateEffect_019e4723-60dc-76a2-b914-b3d9defa32fb" 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_EffectOfExchangeRateOnCashCashEquivalentsRestrictedCashAndRestrictedCashEquivalents_019e4723-60dc-7ce2-89b9-874f90b332ba" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_EffectOfExchangeRateOnCashCashEquivalentsRestrictedCashAndRestrictedCashEquivalents"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalentsPeriodIncreaseDecreaseIncludingExchangeRateEffect_019e4723-60dc-76a2-b914-b3d9defa32fb" xlink:to="loc_us-gaap_EffectOfExchangeRateOnCashCashEquivalentsRestrictedCashAndRestrictedCashEquivalents_019e4723-60dc-7ce2-89b9-874f90b332ba" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NetCashProvidedByUsedInFinancingActivities_019e4723-60dc-773b-8d91-210f820414ad" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_NetCashProvidedByUsedInFinancingActivities"/>
    <link:calculationArc order="2" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalentsPeriodIncreaseDecreaseIncludingExchangeRateEffect_019e4723-60dc-76a2-b914-b3d9defa32fb" xlink:to="loc_us-gaap_NetCashProvidedByUsedInFinancingActivities_019e4723-60dc-773b-8d91-210f820414ad" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NetCashProvidedByUsedInInvestingActivities_019e4723-60dc-774e-ae42-abafa8bd01c8" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_NetCashProvidedByUsedInInvestingActivities"/>
    <link:calculationArc order="3" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalentsPeriodIncreaseDecreaseIncludingExchangeRateEffect_019e4723-60dc-76a2-b914-b3d9defa32fb" xlink:to="loc_us-gaap_NetCashProvidedByUsedInInvestingActivities_019e4723-60dc-774e-ae42-abafa8bd01c8" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NetCashProvidedByUsedInOperatingActivities_019e4723-60dc-7e99-b7f3-09dbe6f2ddc0" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_NetCashProvidedByUsedInOperatingActivities"/>
    <link:calculationArc order="4" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalentsPeriodIncreaseDecreaseIncludingExchangeRateEffect_019e4723-60dc-76a2-b914-b3d9defa32fb" xlink:to="loc_us-gaap_NetCashProvidedByUsedInOperatingActivities_019e4723-60dc-7e99-b7f3-09dbe6f2ddc0" xlink:type="arc"/>
  </link:calculationLink>
  <link:roleRef roleURI="http://www.trupanion.com/role/DebtDetailsScheduleofMaturities" xlink:type="simple" xlink:href="trup-20260630.xsd#DebtDetailsScheduleofMaturities"/>
  <link:calculationLink xlink:role="http://www.trupanion.com/role/DebtDetailsScheduleofMaturities" xlink:type="extended">
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LineOfCredit_019e4723-61b3-786c-9647-941a672c7c92" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_LineOfCredit"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LongTermDebtMaturitiesRepaymentsOfPrincipalInYearTwo_019e4723-61b3-76f9-aaf4-d506d015b81e" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_LongTermDebtMaturitiesRepaymentsOfPrincipalInYearTwo"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_LineOfCredit_019e4723-61b3-786c-9647-941a672c7c92" xlink:to="loc_us-gaap_LongTermDebtMaturitiesRepaymentsOfPrincipalInYearTwo_019e4723-61b3-76f9-aaf4-d506d015b81e" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LongTermDebtMaturitiesRepaymentsOfPrincipalInNextTwelveMonths_019e4723-61b3-74c2-a139-4d437e1e55ec" 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_LineOfCredit_019e4723-61b3-786c-9647-941a672c7c92" xlink:to="loc_us-gaap_LongTermDebtMaturitiesRepaymentsOfPrincipalInNextTwelveMonths_019e4723-61b3-74c2-a139-4d437e1e55ec" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LongTermDebtMaturitiesRepaymentsOfPrincipalInYearThree_019e4723-61b3-7780-b67b-4aad793f48d5" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_LongTermDebtMaturitiesRepaymentsOfPrincipalInYearThree"/>
    <link:calculationArc order="3" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_LineOfCredit_019e4723-61b3-786c-9647-941a672c7c92" xlink:to="loc_us-gaap_LongTermDebtMaturitiesRepaymentsOfPrincipalInYearThree_019e4723-61b3-7780-b67b-4aad793f48d5" xlink:type="arc"/>
  </link:calculationLink>
</link:linkbase>
