144 0001611679 XXXXXXXX LIVE 0001371285 TRUPANION, INC. 001-36537 6100 4TH AVENUE SOUTH SUITE 400 SEATTLE WA 98108 888-733-2685 RAWLINGS DARRYL Director Common Stock Fidelity Brokerage Services LLC

245 Summer Street Boston MA 02110

30369 135794.30 42994675 09/04/2025 NASDAQ Common 11/25/2021 Stock Award Trupanion N 2925 11/25/2021 Compensation Common 02/22/2021 Stock Award Trupanion N 54 02/22/2021 Compensation Common 11/25/2020 Stock Award Trupanion N 2062 11/25/2020 Compensation Common 02/25/2021 Stock Award Trupanion N 6743 02/25/2021 Compensation Common 08/25/2021 Stock Award Trupanion N 2926 08/25/2021 Compensation Common 02/25/2022 Stock Award Trupanion N 11037 02/25/2022 Compensation Common 05/25/2021 Stock Award Trupanion N 2925 05/25/2021 Compensation Common 08/25/2022 Stock Award Trupanion N 3847 08/25/2022 Compensation Common 05/25/2022 Stock Award Trupanion N 3846 05/25/2022 Compensation Common 08/25/2020 Stock Award Trupanion N 2062 08/25/2020 Compensation Common 02/25/2023 Stock Award Trupanion N 7560 02/25/2023 Compensation Common 11/25/2024 Stock Award Trupanion N 6308 11/25/2024 Compensation Common 11/25/2022 Stock Award Trupanion N 3846 11/25/2022 Compensation Common 02/25/2021 Stock option Trupanion N 439 02/25/2021 cash/check Common 11/25/2024 Stock Award Trupanion N 7517 11/25/2024 Compensation Common 11/25/2019 Stock Award Trupanion N 740 11/25/2019 Compensation Common 11/25/2020 Stock Award Trupanion N 2062 11/25/2020 Compensation Common 02/25/2020 Stock Award Trupanion N 5382 02/25/2020 Compensation Common 02/25/2025 Stock Award Trupanion N 3684 02/25/2025 Compensation Common 05/25/2019 Stock Award Trupanion N 740 05/25/2019 Compensation Common 08/25/2023 Stock Award Trupanion N 4376 08/25/2023 Compensation Common 02/25/2019 Stock Award Trupanion N 2959 02/25/2019 Compensation Common 02/22/2025 Stock Award Trupanion N 7500 02/22/2025 Compensation Common 11/25/2023 Stock Award Trupanion N 4259 11/25/2023 Compensation Common 11/19/2018 Stock Award Trupanion N 100477 11/19/2018 Compensation Common 11/12/2018 Stock Award Trupanion N 100477 11/12/2018 Compensation Common 08/25/2019 Stock Award Trupanion N 740 08/25/2019 Compensation N RAWLINGS DARRYL

6100 4TH AVENUE SOUTH STE 400 Seattle WA 98108

Common stock 09/03/2025 19631 878487.25 shares are being sold form Kuyashii Primary Equities LLC 09/04/2025 /s/ Jason Coleman as a duly authorized representative of Fidelity Brokerage Services LLC, as attorney-in-fact for Darryl RAWLINGS