X0609 4 2026-08-22 0 0001371285 TRUPANION, INC. TRUP 0001622728 BEARMAN ASHER false C/O TRUPANION, INC. 6100 4TH AVENUE S, SUITE 200 SEATTLE WA 98108 0 1 0 0 Chief Legal Officer 0 Common Stock 2026-08-22 4 M 0 265 A 72509 D Common Stock 2026-08-22 4 F 0 86 31.76 D 72423 D Common Stock 2026-08-22 4 M 0 9 A 72432 D Common Stock 2026-08-22 4 F 0 2 31.76 D 72430 D Common Stock 2026-08-22 4 M 0 379 A 72809 D Common Stock 2026-08-22 4 F 0 123 31.76 D 72686 D Common Stock 2026-08-22 4 M 0 1832 A 74518 D Common Stock 2026-08-22 4 F 0 590 31.76 D 73928 D Common Stock 2026-08-25 4 M 0 125 A 74053 D Common Stock 2026-08-25 4 F 0 40 31.84 D 74013 D Restricted Stock Unit (RSU) 2026-08-22 4 M 0 265 0 D 2027-02-22 Common Stock 265 531 D Restricted Stock Unit (RSU) 2026-08-22 4 M 0 9 0 D 2027-02-22 Common Stock 9 18 D Restricted Stock Unit (RSU) 2026-08-22 4 M 0 379 0 D 2027-08-22 Common Stock 379 1516 D Restricted Stock Unit (RSU) 2026-08-22 4 M 0 1832 0 D 2028-02-22 Common Stock 1832 10992 D Restricted Stock Unit (RSU) 2026-08-25 4 M 0 125 0 D 2027-08-25 Common Stock 125 500 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 2,122 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, 2025, the reporting person was granted 70 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 August 15, 2025, the reporting person was granted 3,032 restricted stock units (RSUs). The RSUs vest and convert into common stock of the Issuer as to 1/8th of the total shares on November 22, 2025, after which 1/8th of the total shares vest quarterly, subject to continued service through each vest date. On February 20, 2026, the reporting person was granted 14,656 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 August 14, 2023, the Reporting Person was granted 1,999 restricted stock units (RSUs). The RSUs vest and will convert to common stock of the Issuer as to 1/4th of the total shares on August 25, 2024, after which 1/16th of the total shares vest quarterly, subject to continued service through each vest date. /s/ Lauren Welsh as attorney-in-fact for Asher Bearman 2026-08-26