#1May 2023 Trupanion Investor Presentation#2This presentation contains forward-looking statements within the meaning of Section 27A of the Securities Act of 1933 and Section 21E of the Securities Exchange Act of 1934 relating to, among other things, expectations, plans, prospects and financial results for Trupanion, including, but not limited to, its expectations regarding its ability to execute its business plans. These forward-looking statements are based upon the current expectations and beliefs of Trupanion's management as of the date of this presentation, and are subject to certain risks and uncertainties that could cause actual results to differ materially from those described in the forward-looking statements. All forward-looking statements made in this presentation are based on information available to Trupanion as of the date hereof, and Trupanion has no obligation to update these forward- looking statements. In particular, the following factors, among others, could cause results to differ materially from those expressed or implied by such forward-looking statements: 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 implement and maintain effective controls, including over financial reporting; the ability to protect and enforce Trupanion's intellectual property rights; 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; and our ability to retain key personnel. For a detailed discussion of these and other cautionary statements, please refer to the risk factors discussed in filings with the Securities and Exchange Commission (SEC), including but not limited to, Trupanion's Annual Report on Form 10-K for the year ended December 31, 2022 and any subsequently filed reports on Forms 10-Q and 8-K. All documents are available through the SEC's Electronic Data Gathering Analysis and Retrieval system at www.sec.gov or the Investor Relations section of Trupanion's website at http://investors.trupanion.com. In addition to U.S. GAAP financials, this presentation includes certain non-GAAP financial measures. These non-GAAP measures are in addition to, not a substitute for or superior to, measures of financial performance prepared in accordance with U.S. GAAP. A reconciliation of non-GAAP financial measures to the corresponding GAAP measures is provided on our Investor Relations website. trupanion™#3Growth company Market Economics Moats Financials Position Large, underpenetrated market Compounding, monthly recurring cash flow. Difficult to replicate with foundation to build 20%+ revenue growth & strong returns on invested capital Leading the category, industry leading retention trupanion™ 3#4Who We Are Trupanion exists to help loving, responsible pet owners budget & care for their pets. trupanion™ 4#5Why Trupanion Broadest coverage Best Value Customer Service Comprehensive, lifelong coverage if pet becomes sick or injured Freedom to choose any veterinarian, emergency care, or specialty hospital Covers hereditary and congenital conditions . No birthday pricing, unique to industry 71% claims payout 90% of covered veterinary costs No payout limits Only brand with software enabling direct payment to veterinarian at time of checkout 24/7 customer service Significant veterinary hospital experience across organization 5#6Cost of Care Trupanion Eliminates Uncertainty Around Very lucky pets subsidize JE 70% unlucky pets 50% Average pet 100% + trupanion™ 6#7Large, Underpenetrated Markets LARGE, UNDERPENETRATED MARKETS (1), (2), (3), (4) 12% 7% 7% 8% 9% 3% 3% France Switzerland Netherlands Australia Japan + T 7 7 7 7 7 7 ) -2% Slovakia Czech Republic 1234 North America Germany Kynetec on behalf of the Canadian Animal Health Institute, CAHI Estimate of Canadian Dog and Cat Population Survey, 2016. Packaged Facts, a division of Market Research Group, LLC, Pet Insurance in North America, 5th Edition, September 2018. Munich RE, How to Unlock the Potential of Pet Health?, May 2013. Unless otherwise noted, based on company sources and estimates. U.K. 25% Sweden 67% trupanion™ 7#8Estimated Market Opportunity 200M cats and dogs in North America 120M visit the veterinarian every year 12M puppies and kittens born each year 1M new pet leads per month trupanion™ 8#9Estimated Market Opportunity 1,000,000 puppies and kittens per month visiting veterinarians ÷ 25,000 veterinary hospitals in North Americal = 40 new puppies and kittens per hospital, per month trupanion™ 9#10Pet Medical Insurance is a growing $1B+ category! ($ in billions) 24% Industry Revenue CAGR $2.84 $2.17 $1.72 $1.39 $1.16 $0.77 $0.94 $3.51 2015 2016 2017 2018 2019 2020 2021 2022 Source: NAPHIA 2023 State of the Industry Report. North America Gross Written Premiums in USD. trupanion™ 10#11Trupanion is the growth leader in North America Industry revenue was $3.5B in 2022, up 24% YOY •The industry added $670M in revenue in 2022, consistent with the prior year . • In 2022, Trupanion Inc. was the largest contributor of the category's growth at 29% and was the largest provider of medical insurance for pets in North America trupanion™ 11#12Growing our Global Footprint trupanion trupanion PHIDIRECT Fluff-free Pet Health Insurance Furkin PET INSURANCE As of December 31, 2022 = NV trupanion#13Defensible Moats Deep Veterinary Relationships Superior Value Proposition Data Driven Advantage Patented, Automated & Direct Veterinary Invoice Payment trupanion™ 13#14$0 Q1 '10 $50.0 $100.0 $150.0 Q2'10 Q3'10 Q4'10 Q1'11 Q2'11 Q3'11 Q4'11 $200.0 Q1 '12 Q2'12 $250.0 $300.0 Total Revenue Growth ($ in millions) $3.1 $4.4 $5.3 $6.3 $7.6 $8.8 $9.9 $10.7 $12.0 $13.2 $14.5 $15.9 $17.8 $19.8 $22.1 $24.0 $25.6 $28.1 $30.3 $31.9 $33.3 $35.6 $37.9 $40.2 $42.7 $45.8 $48.4 $51.3 $54.7* Q3'12 Q4'12 Q1 '13 Q2'13 Q3'13 Q4'13 Q1 '14 Q2'14 Q3'14 Q4'14 Q1 '15 ■Revenue from Existing Pets Q2'15 Q3'15 Q4'15 Q1 '16 Q2'16 Q3'16 Q4'16 ■Revenue from New Pets Q1 '17 Q2'17 Q3'17 Q4'17 Q1 '18 $256.3 $246.0 $233.8 $219.4 $206.0 $194.4 $181.7 $168.3 $154.7 $142.7 $130.1 $117.9 $111.3 $105.5 $99.3 $92.2 $87.0 $82.6 $78.2 $63.1 $69.8 $66.6 $73.4 $58.3 Q2'18 Q3'18 Q4'18 Miscellaneous Revenue Q1 '19 Total Q2'19 Q3'19 Q4'19 Q1'20 Q2'20 Q3 '20 Q4'20 Q1'21 Q2'21 Q3 '21 Q4'21 Q1'22 Q2'22 Q3 '22 Q4'22 Q1'23 trupanion™ 14#15$280.0 $260.0 Revenue By Cohort $240.0 $220.0 $200.0 AVERAGE MONTHLY RETENTION; 98.65% (1) $180.0 $160.0 $140.0 $120.0 $100.0 $80.0 $60.0 $40.0 $20.0 2010Q1 (20.0) 2011Q1 2012Q1 2013Q1 2014Q1 2015Q1 2016Q1 2017Q1 2018Q1 2019Q1 2020Q1 2021Q1 ■Pre-2010 ■ 2010 2011 2012 2013 ■2014 2015 2016 2017 2018 2019 ■2020 2021 2022 2023 ■Other Business 1. For the 12-month period ended March 31, 2023. Average monthly retention is calculated as the monthly retention rate of enrolled subscription pets for each applicable. period averaged over the 12 months prior to the period end date. 2022Q1 2023Q1 trupanion™ 15#16Unit Economics¹ - Single Ave. Subscription Pet Monthly ARPU $63.67 Paying Veterinary Invoices. (47.35) Variable Expenses (providing 24/7 fast service) (6.26) Fixed Expenses (G&A + IT) (2.75) Cash generated per month, prior to capital charge Capital Charge³ Cash generated per month 2) Metrics presented on a trailing twelve month basis for the period ended 3.31.23 Calculated as 1/monthly churn. Estimated at 1% of ARPU. $7.31 x 74.1 months2 = $541 LVP, incl fixed expenses (0.64) $6.67 x 74.1 months2 = $494 trupanion™ 16#17Growth Levers . Number of stores in North America Same-store-sales Different subscription offerings • Adjunct business lines. • International markets MORE LEADS HIGHER CONVERSION MORE COVERAGE LESS COVERAGE DIFFERENT CHANNELS OTHER PET SUBSCRIPTION PRODUCTS (WHERE WE HAVE COMPETITIVE ADVANTAGE) 50K+ HOSPITALS TARGET trupanion™ 17#18Returns on Invested Capital 30% internal rate of return $247 $541 1 Pet Acquisition Cost $0 $100 $200 15 1) 2) PAC as of the three month period ended 3.31.2023 Estimated cash flows prior to new pet acquisition. Average Expected Cash Flow per Pet 2 $300 $400 $500 $600 trupanion™ 18#19Margin Profile 1. $ in millions Revenue Subscription Business Other Business Q1'22 Q1'23 Q1'22 Q1'23 $139.8 $165.2 $66.2 $91.1 Total Q1'22 Q1'23 $206.0 $256.3 24.4% Cost of Goods $99.4 $128.1 $44.3 $65.1 $143.8 $193.3 Variable Expenses $14.0 $16.7 $16.5 $18.7 $30.5 $35.4 Fixed Expenses $6.9 $7.8 $3.2 $4.3 $10.1 $12.1 Adjusted Operating Income $19.5 $12.6 $2.1 $2.9 $21.6 $15.5 -28.0% Acquisition Cost $19.2 $19.6 $0.1 $0.1 $19.3 $19.6 Adjusted EBITDA Free Cash Flow $1.2 -$4.9 -$7.1 -$12.0 Net Subscription Pets Added 32,358 36,507 12.8% % of revenue Subscription Business Other Business Total Q1'22 Q1'23 Target Q1'22 Q1'23 Q1'22 Q1'23 Revenue 100% 100% 100% 100% 100% 100% 100% Cost of Goods 71.1% 77.6% 71.0% 67.0% 71.5% 69.8% 75.4% Variable Expenses 10.0% 10.1% 9.0% 24.9% 20.6% 14.8% 13.8% Fixed Expenses 4.9% 4.7% 5.0% 4.9% 4.7% 4.9% 4.7% Adjusted Operating Margin 14.0% 7.6% 15.0% 3.1% 3.2% 10.5% 6.1% Internal Rate of Return 34% 30% 30-40% Note: The above table includes non-GAAP financial measures. For more information about our non-GAAP financial measures, see "Supplemental Financial Information" in the IR section of Trupanion's website. 2. * Fixed expenses reflect the performance of each segment using a pro-rata expense allocation based on revenues trupanion™ 19#20Questions? Thank you.