X0508 4 2025-11-24 0 0001371285 TRUPANION, INC. TRUP 0001966925 MCGIBNEY BRENNA 309-1277 LYNN VALLEY ROAD NORTH VANCOUVER A1 V7J 0A2 BRITISH COLUMBIA, CANADA 0 1 0 0 Chief Administration Officer 0 Common Stock 2025-11-24 4 M 0 1354 A 5059 D Common Stock 2025-11-24 4 F 0 724 35.40 D 4335 D Common Stock 2025-11-24 4 M 0 1250 A 5585 D Common Stock 2025-11-24 4 F 0 669 35.40 D 4916 D Common Stock 2025-11-24 4 M 0 1881 A 6797 D Common Stock 2025-11-24 4 F 0 1006 35.40 D 5791 D Restricted Stock Unit (RSU) 2025-11-24 4 M 0 1354 0 D 2026-02-22 Common Stock 1354 1354 D Restricted Stock Unit (RSU) 2025-11-24 4 M 0 1250 0 D 2028-02-25 Common Stock 1250 11250 D Restricted Stock Unit (RSU) 2025-11-24 4 M 0 1881 0 D 2027-02-22 Common Stock 1881 9409 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, 2024, the reporting person was granted 10,829 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 20,000 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. On February 27, 2025, the reporting person was granted 15,053 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. /s/ Christina Poler as attorney-in-fact for Brenna McGibney 2025-11-25