JOHN R. GALLAGHER - 20 Feb 2026 Form 4 Insider Report for TRUPANION, INC. (TRUP)

Role: Chief Operating Officer
Signature: /s/ Lauren Welsh as attorney-in-fact for John R. Gallagher
Issuer symbol: TRUP
Transactions as of: 20 Feb 2026
Net transactions value: -$51,821
Form type: 4
Filing time: 24 Feb 2026, 21:11:16 UTC
Previous filing: 29 Jan 2026
Next filing: 27 Feb 2026
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/ Lauren Welsh as attorney-in-fact for John R. Gallagher	24 Feb 2026	0001967117

Transactions Table

Type	Sym	Class	Transaction	Value $	Shares	Change %	* Price $	Shares After	Date	Ownership	Footnotes
transaction	TRUP	Common Stock	Options Exercise		+2,570	+8.1%		34,431	22 Feb 2026	Direct	F1
transaction	TRUP	Common Stock	Tax liability	$20,696	-762	-2.2%	$27.16	33,669	22 Feb 2026	Direct	F2
transaction	TRUP	Common Stock	Options Exercise		+864	+2.6%		34,533	22 Feb 2026	Direct	F1
transaction	TRUP	Common Stock	Tax liability	$5,704	-210	-0.61%	$27.16	34,323	22 Feb 2026	Direct	F2
transaction	TRUP	Common Stock	Options Exercise		+3,327	+9.7%		37,650	22 Feb 2026	Direct	F1
transaction	TRUP	Common Stock	Tax liability	$25,422	-936	-2.5%	$27.16	36,714	22 Feb 2026	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)	Award	$0	+16,609		$0.000000	16,609	20 Feb 2026	Common Stock	16,609		Direct	F1, F3
transaction	TRUP	Restricted Stock Unit (RSU)	Options Exercise	$0	-2,570	-100%	$0.000000	0	22 Feb 2026	Common Stock	2,570		Direct	F1, F4
transaction	TRUP	Restricted Stock Unit (RSU)	Options Exercise	$0	-864	-8.3%	$0.000000	9,514	22 Feb 2026	Common Stock	864		Direct	F1, F5
transaction	TRUP	Restricted Stock Unit (RSU)	Options Exercise	$0	-3,327	-20%	$0.000000	13,310	22 Feb 2026	Common Stock	3,327		Direct	F1, F6

* An asterisk sign (*) next to the price indicates that the price is likely invalid.

Explanation of Responses:

Id	Content
F1	Restricted stock units 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 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.
F4	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.
F5	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.
F6	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.