X0508 4 2025-11-24 0 0001371285 TRUPANION, INC. TRUP 0001966923 WHEELER SIMON 4TH FLOOR CHARTER HOUSE WOODLANDS ROAD ALTRINCHAM X0 WA14 1HF UNITED KINGDOM 0 1 0 0 EVP, Trupanion International 0 Common Stock 2025-11-24 4 M 0 528 A 19583 D Common Stock 2025-11-24 4 F 0 248 35.40 D 19335 D Common Stock 2025-11-24 4 M 0 937 A 20272 D Common Stock 2025-11-24 4 F 0 440 35.40 D 19832 D Common Stock 2025-11-24 4 M 0 1525 A 21357 D Common Stock 2025-11-24 4 F 0 716 35.40 D 20641 D Restricted Stock Unit (RSU) 2025-11-24 4 M 0 528 0 D 2027-02-22 Common Stock 528 2637 D Restricted Stock Unit (RSU) 2025-11-24 4 M 0 937 0 D 2026-02-22 Common Stock 937 2114 D Restricted Stock Unit (RSU) 2025-11-24 4 M 0 1525 0 D 2028-02-25 Common Stock 1525 7850 D Restricted stock units convert into common stock on a one-for-one basis. This Form 4 discloses the shares of common stock that have been withheld by the issuer to satisfy its income tax withholding and remittance obligations in connection with the vesting of the restricted stock units, and does not represent a sale by the reporting person. On February 27, 2025, the reporting person was granted 4,219 restricted stock units (RSUs). The RSUs vest and convert into common stock of the Issuer as to 1/8th of the total shares on May 22, 2025, after which 1/8th of the total shares vest quarterly, subject to continued service through each vest date. On February 27, 2024, the reporting person was granted 12,203 restricted stock units (RSUs). The RSUs vest and convert into common stock of the Issuer as to 1/8th of the total shares on May 22, 2024, after which 1/8th of the total shares vest quarterly, subject to continued service through each vest date. On February 27, 2024, the reporting person was granted 15,000 restricted stock units (RSUs). The RSUs vest and convert into common stock of the Issuer as to 1/4th of the total shares on February 25, 2025, after which 1/16th of the total shares vest quarterly, subject to continued service through each vest date. /s/ Christina Poler as attorney-in-fact for Simon Wheeler 2025-11-25