X0508 4 2026-02-20 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 0 Common Stock 2026-02-22 4 M 0 2570 A 34431 D Common Stock 2026-02-22 4 F 0 762 27.16 D 33669 D Common Stock 2026-02-22 4 M 0 864 A 34533 D Common Stock 2026-02-22 4 F 0 210 27.16 D 34323 D Common Stock 2026-02-22 4 M 0 3327 A 37650 D Common Stock 2026-02-22 4 F 0 936 27.16 D 36714 D Restricted Stock Unit (RSU) 2026-02-20 4 A 0 16609 0 A 2028-02-22 Common Stock 16609 16609 D Restricted Stock Unit (RSU) 2026-02-22 4 M 0 2570 0 D 2026-02-22 Common Stock 2570 0 D Restricted Stock Unit (RSU) 2026-02-22 4 M 0 864 0 D 2028-11-22 Common Stock 864 9514 D Restricted Stock Unit (RSU) 2026-02-22 4 M 0 3327 0 D 2027-02-22 Common Stock 3327 13310 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 20, 2026, the reporting person was granted 16,609 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, 2026, 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 20,559 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 November 12, 2024, the reporting person was granted 13,838 restricted stock units (RSUs). The RSUs vest and convert into common stock of the Issuer as to 1/4th of the total shares on November 22, 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 26,619 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/ Lauren Welsh as attorney-in-fact for John R. Gallagher 2026-02-24