X0508 4 2025-10-27 0 0001371285 TRUPANION, INC. TRUP 0001657025 Tooth Margaret C/O TRUPANION, INC. 6100 4TH AVENUE SOUTH, SUITE 200 SEATTLE WA 98108 1 1 0 0 CEO 1 Common Stock 2025-10-27 4 M 0 6000 8.93 A 150229 D Common Stock 2025-10-27 4 S 0 6000 43.7233 D 144229 D Common Stock 2025-10-27 4 S 0 2884 43.7424 D 141345 D Stock Option (right to buy) 8.93 2025-10-27 4 M 0 6000 0 D 2025-12-21 Common Stock 6000 16000 D The exercise and sale reported were effected pursuant to a Rule 10b5-1 trading plan adopted by reporting person on June 6, 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 $43.4200 to $44.0500 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). The reported price in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $43.5700 to $44.0500 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 (3). This stock option grant is fully vested. /s/ Christina Poler as attorney-in-fact for Margaret Tooth 2025-10-29