TRUP Q3 2025 Earnings Presentation

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Quarterly Earnings Supplement Q3 2025

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Total Subscription Revenue Growth $3.1 $4.4 $5.3 $6.3 $7.6 $8.8 $9.9 $10.7 $12.0 $13.2 $14.5 $15.7 $17.0 $18.4 $20.0 $21.4 $22.9 $24.9 $27.1 $28.6 $30.1 $32.2 $34.4 $36.7 $39.1 $42.2 $44.6 $47.4 $50.2 $52.6 $56.5 $59.0 $61.5 $63.9 $67.4 $70.9 $74.2 $77.7 $82.6 $86.6 $89.5 $92.5 $99.4 $106.4 $113.3 $120.4 $127.1 $134.1 $139.8 $145.8 $152.4 $158.6 $165.2 $173.3 $182.9 $191.5 $201.1 $208.6 $219.0 $227.8 $233.1 $242.2 $252.7 $0 $50.0 $100.0 $150.0 $200.0 $250.0 $300.0 ($ in millions) Revenue from Existing Subscription Pets Revenue from New Subscription Pets Miscellaneous Revenue 20152010 2011 2012 2013 2014 202520242022 20232016 2017 2018 2019 2020 2021

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Subscription Revenue By Cohort - $20.0 $40.0 $60.0 $80.0 $100.0 $120.0 $140.0 $160.0 $180.0 $200.0 $220.0 $240.0 $260.0 $280.0 ($ in millions) Pre-2010 2010 2011 2012 2013 2014 2015 2016 2017 2018 2019 2020 2021 2022 2023 2024 2025 20152010 2011 2012 2013 2014 202520242022 20232016 2017 2018 2019 2020 2021

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Subscription Segment Trupanion Core North America Other Subscription Products North America PHI Direct Furkin Chewy Aflac Other Subscription Products Europe PetExpert* (Czechia, Slovakia, Belgium, Poland) Smart Paws (Germany, Switzerland) Trupanion (Germany, Switzerland) Product Offerings Other Business Segment Pets Best Veteran Affairs Service Dog Program Legacy Worksite Benefits (Corporate & Veterinary Hospital) *Managing General Agents (insurance commission revenue). We intend to transition these products to a Trupanion branded produc t over time

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Subscription Pet Count Q3 2025 Q2 2025 Q1 2025 Q4 2024 Q3 2024 Gross new pets 68,111 62,740 63,661 60,162 65,753 Core Trupanion 57,671 53,186 53,611 51,331 55,667 Other Subscription North America 5,845 5,569 6,018 5,309 6,369 Other Subscription Europe 4,595 3,985 4,032 3,522 3,717 Total subscription pets enrolled (at period end) 1,082,412 1,066,354 1,052,845 1,041,212 1,032,042 Excluding MGA pets enrolled 1,026,780 1,014,251 1,003,732 994,072 983,452

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Definitions – Estimated IRR • Average revenue per new pet. Average revenue per new pet is calculated from total premium for all new pets enrolled for the period divided by the total number of new subscription pet months in the period. Total new subscription pet months in a period represents the sum of all new subscription pets enrolled for each month during the period. • Margin per pet. Margin per pet is calculated based on subscription revenue less cost of revenue from our subscription business segment for the 36 months prior to the period end date excluding stock- based compensation expense, sign-up fee revenue and the change in deferred revenue between periods. This amount is also reduced by the fixed expenses related to our subscription business, less stock-based compensation, based on revenues. The percent margin of this profit is multiplied by quarterly average revenue per new pet. • Lifetime value of a pet, including fixed expenses. Lifetime value of a pet, including fixed expenses, is calculated based on subscription revenue less cost of revenue from our subscription business segment for the 36 months prior to the period end date excluding stock-based compensation expense related to cost of revenue from our subscription business segment, sign-up fee revenue and the change in deferred revenue between periods. This amount is also reduced by the fixed expenses related to our subscription business, which are the pro-rata portion of general and administrative and technology expenses, less stock-based compensation, based on revenues. This amount, on a per pet basis, is multiplied by the implied average subscriber life in months. Implied average subscriber life in months is calculated as the quotient obtained by dividing one by one minus the average monthly retention rate over the past 36 months. We monitor lifetime value of a pet, including fixed expenses, to estimate the value we might expect from new pets over their implied average subscriber life in months, if they behave like the average pet in that respective period. When evaluating the amount of pet acquisition expenses we may want to incur to attract new pet enrollments, we refer to the lifetime value of a pet, including fixed expenses, as well as our estimated internal rate of return calculation for an average pet, which also includes an estimated surplus capital charge, to inform the amount of acquisition spend in relation to the estimated payback period. • Average pet acquisition cost. Average pet acquisition cost (PAC) is calculated as net acquisition cost divided by the total number of new subscription pets enrolled in that period. Net acquisition cost, a non-GAAP financial measure, is calculated in a reporting period as new pet acquisition expense, excluding stock-based compensation expense, other business segment expense, offset by sign-up fee revenue. We exclude stock-based compensation expense because the amount varies from period to period based on number of awards issued and market-based valuation inputs. We offset sign-up fee revenue because it is a one-time charge to new members collected at the time of enrollment used to partially offset initial setup costs, which are included in new pet acquisition expenses. We exclude other business segment pet acquisition expense because that does not relate to subscription enrollments. We monitor average pet acquisition cost to evaluate the efficiency in acquiring new members and measure effectiveness based on our targeted return on investment. • Internal rate of return per average subscription pet (IRR) is calculated assuming the new subscription pets we enroll during the period will behave like an average subscription pet over the last 36 months, and represents the discount rate that results in the net present value of all estimated future cash flows generated over an average enrolled pet’s implied subscriber life, to be equal to zero. Cash outflows from an average pet include average pet acquisition cost for the applicable period. Cash outflows also include a monthly capital charge, which we estimate as 1% of the average quarterly revenue per new pet. Cash inflows from an average pet calculated based margin per pet multiplied by average revenue per new pet for the applicable period. • Trailing 3-year Retention. Trailing 3-year retention is measured as the monthly retention rate of enrolled subscription pets for each applicable period averaged over the 36 months prior to the period end date. As such, our average monthly retention rate as of September 30, 2025 is an average of each month’s retention from October 1, 2022 through September 30, 2025. We calculate monthly retention as the number of pets that remain after subtracting all pets that cancel during a month, including pets that enroll and cancel within that month, divided by the total pets enrolled at the beginning of that month.

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Disclaimers Forward-Looking Statements Average All information under the heading “Outlook” in this Quarterly Earnings Supplement is a forward-looking statement. Such statements are subject to risks and uncertainties that could cause actual results to differ materially, including: the ability to achieve or maintain profitability and/or appropriate levels of cash flow in future periods; the ability to keep growing our membership base and revenue; the accuracy of assumptions used in determining appropriate member acquisition expenditures; the severity and frequency of claims; the ability to maintain high retention rates; the accuracy of assumptions used in pricing medical plan subscriptions and the ability to accurately estimate the impact of new products or offerings on claims frequency; actual claims expense exceeding estimates; regulatory and other constraints on the ability to institute, or the decision to otherwise delay, pricing modifications in response to changes in actual or estimated claims expense; the effectiveness and statutory or regulatory compliance of our Territory Partner model and of our Territory Partners, veterinarians and other third parties in recommending medical plan subscriptions to potential members; the ability to retain existing Territory Partners and increase the number of Territory Partners and active hospitals; compliance by us and those referring us members with laws and regulations that apply to our business, including the sale of a pet medical plan; the ability to maintain the security of our data; fluctuations in the Canadian currency exchange rate; the ability to protect our proprietary and member information; the ability to maintain our culture and team; the ability to maintain the requisite amount of risk-based capital; our ability to generate sufficient cash flows to repay or otherwise comply with requirements of our outstanding debt; our ability to implement and maintain effective controls, including to remediate material weaknesses in internal controls over financial reporting; the ability to protect and enforce Trupanion’s intellectual property rights; the ability to successfully implement our alliance with Aflac; our ability to successfully finalize the transition of policies from Accelerant to our wholly owned subsidiary, GPIC; the ability to continue key contractual relationships with third parties; third-party claims including litigation and regulatory actions; the ability to recognize benefits from investments in new solutions and enhancements to Trupanion’s technology platform and website; our ability to retain key personnel; and deliberations and determinations by the Trupanion board based on the future performance of the company or otherwise. For a detailed discussion of these risks and uncertainties, please refer to the risk factors and other disclosure contained in our most recent Form 10-K and subsequent Forms 10-Q and 8-K filed with the SEC from time to time. These forward-looking statements are based upon the current expectations and beliefs of Trupanion’s management as of the date hereof, and Trupanion assumes no obligation to update these forward-looking statements, except as required by law. Non-GAAP Financial Measures This Quarterly Earnings Supplement contains non-GAAP information, including average pet acquisition cost and free cash flow. See the Non-GAAP disclosures and reconciliations in Trupanion's Form 10-Q and earnings release announcing results for the third quarter of 2025.

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