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 FIDELITY BROKERAGE SERVICES LLC

245 SUMMER STREET Boston MA 02210

24000 1129920.00 42490664 05/16/2025 NASDAQ Common 04/20/2007 Founders Shares n/a N 24000 04/20/2007 n/a N Montgomery Holdings Trust

6100 4th Avenue,S suite 200 Seattle WA 98108

TRUP 03/05/2025 2000 67348.12 Wilson Holding Trust

6100 4th Avenue,S suite 200, Seattle WA 98108

TRUP 03/05/2025 2000 67198.33 12,000 shares sold from Montgomery Holdings Trust and 12,000 shares sold from Wilson Holding Trust where Joseph Tappan is signing as trustee but form 144 will be filed under Darryl Rawlings credentials since children are underage and live at home. 05/16/2025 Carmen Zamores as a duly authorized representative of Fidelity Brokerage Services LLC, as attorney-in-fact for RAWLINGS DARRYL