John R. Gallagher - 25 Aug 2025 Form 4 Insider Report for TRUPANION, INC. (TRUP)

Role
Chief Operating Officer
Signature
/s/ Christina Poler as attorney-in-fact for John R. Gallagher
Issuer symbol
TRUP
Transactions as of
25 Aug 2025
Net transactions value
-$13,886
Form type
4
Filing time
27 Aug 2025, 21:30:05 UTC
Previous filing
26 Aug 2025
Next filing
25 Nov 2025
SEC
View on sec.gov

Reporting Owners (1)

Name Relationship Address Signature Signature date CIK
GALLAGHER JOHN R Chief Operating Officer 6100 4TH AVENUE S, SUITE 200, SEATTLE /s/ Christina Poler as attorney-in-fact for John R. Gallagher 27 Aug 2025 0001967117

Transactions Table

Type Sym Class Transaction Value $ Shares Change % * Price $ Shares After Date Ownership Footnotes
transaction TRUP Common Stock Options Exercise +28 +0.09% 31,456 25 Aug 2025 Direct F1
transaction TRUP Common Stock Tax liability $275 -6 -0.02% $45.83 31,450 25 Aug 2025 Direct F2
transaction TRUP Common Stock Options Exercise +735 +2.3% 32,185 25 Aug 2025 Direct F1
transaction TRUP Common Stock Tax liability $8,158 -178 -0.55% $45.83 32,007 25 Aug 2025 Direct F2
transaction TRUP Common Stock Options Exercise +451 +1.4% 32,458 25 Aug 2025 Direct F1
transaction TRUP Common Stock Tax liability $4,995 -109 -0.34% $45.83 32,349 25 Aug 2025 Direct F2
transaction TRUP Common Stock Options Exercise +45 +0.14% 32,394 25 Aug 2025 Direct F1
transaction TRUP Common Stock Tax liability $458 -10 -0.03% $45.83 32,384 25 Aug 2025 Direct F2

Derivative Securities (e.g., puts, calls, warrants, options, convertible securities)

Type Sym Class Transaction Value $ Shares Change % * Price $ Shares After Date Underlying Class Amount Exercise Price Ownership Footnotes
transaction TRUP Restricted Stock Unit (RSU) Options Exercise $0 -28 -12% $0.000000 202 25 Aug 2025 Common Stock 28 Direct F1, F3
transaction TRUP Restricted Stock Unit (RSU) Options Exercise $0 -735 -33% $0.000000 1,469 25 Aug 2025 Common Stock 735 Direct F4, F5
transaction TRUP Restricted Stock Unit (RSU) Options Exercise $0 -451 -11% $0.000000 3,612 25 Aug 2025 Common Stock 451 Direct F4, F6
transaction TRUP Restricted Stock Unit (RSU) Options Exercise $0 -45 -11% $0.000000 360 25 Aug 2025 Common Stock 45 Direct F4, F7
* An asterisk sign (*) next to the price indicates that the price is likely invalid.

Explanation of Responses:

Id Content
F1 The RSUs convert into common stock on a one-for-one basis.
F2 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.
F3 On May 15, 2023, the reporting person was granted 460 restricted stock units (RSUs). The RSUs vested and converted into common stock of the Issuer as to 1/4th of the total shares on May 25, 2024, after which 1/16th of the total shares vest quarterly, subject to continued service through each vest date.
F4 Restricted stock units convert into common stock on a one-for-one basis.
F5 On February 28, 2022, the reporting person was granted 11,752 restricted stock units (RSUs). The RSUs vested and converted into common stock of the Issuer as to 1/4th of the total shares on February 25, 2023, after which 1/16th of the total shares vest quarterly, subject to continued service through each vest date.
F6 On August 14, 2023, the reporting person was granted 7,223 restricted stock units (RSUs). The RSUs vest and convert into 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.
F7 On August 14, 2023, the reporting person was granted 721 restricted stock units (RSUs). The RSUs vest and convert into 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.