X0508 4 2025-11-28 0 0001371285 TRUPANION, INC. TRUP 0001967117 GALLAGHER JOHN R 6100 4TH AVENUE S SUITE 200 SEATTLE WA 98108 0 1 0 0 Chief Operating Officer 1 Common Stock 2025-11-28 4 S 0 6383 34.8242 D 32721 D The sale reported was effected pursuant to a Rule 10b5-1 trading plan adopted by reporting person on August 20, 2025, in order to implement a plan of financial diversification. Accordingly, the reporting person had no discretion with regard to the timing of the transaction. The reported price in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $34.6500 to $35.1800 per share, inclusive. The reporting person undertakes to provide to the issuer, any security holder of the issuer, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the range set forth in this footnote (2). /s/ Christina Poler as attorney-in-fact for John R. Gallagher 2025-12-01