TRUP insider John Gallagher boosts equity stake via RSU vesting

Rhea-AI Filing Summary

Trupanion, Inc. (TRUP) Chief Operating Officer John R. Gallagher reported equity compensation activity involving restricted stock units and related tax withholding. On November 24, 2025, multiple restricted stock unit (RSU) awards converted into common stock, adding blocks of 3,328, 2,570, and 3,460 shares. The company withheld 1,309, 735, and 1,361 shares at a price of $35.4 per share to cover tax obligations, which the filing notes is not a sale by the executive. After these transactions, Gallagher directly owned 38,337 shares of Trupanion common stock. The RSUs stem from prior grants of 26,619, 20,559, and 13,838 units that vest over time, contingent on continued service.

Insider Trade Summary

9,358 shares exercised/converted

Mixed 9 txns

Insider GALLAGHER JOHN R

Role Chief Operating Officer

Type	Security	Shares	Price	Value
Exercise	Restricted Stock Unit (RSU)	3,328	$0.00	--
Exercise	Restricted Stock Unit (RSU)	2,570	$0.00	--
Exercise	Restricted Stock Unit (RSU)	3,460	$0.00	--
Exercise	Common Stock	3,328	$0.00	--
Tax Withholding	Common Stock	1,309	$35.40	$46K
Exercise	Common Stock	2,570	$0.00	--
Tax Withholding	Common Stock	735	$35.40	$26K
Exercise	Common Stock	3,460	$0.00	--
Tax Withholding	Common Stock	1,361	$35.40	$48K

Holdings After Transaction: Restricted Stock Unit (RSU) — 16,637 shares (Direct); Common Stock — 35,712 shares (Direct)

Footnotes (1)

1. 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 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. 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. 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.

Form 4 Insider Transactions: What Each Field Means →

SEC Form 4

FORM 4

UNITED STATES SECURITIES AND EXCHANGE COMMISSION
Washington, D.C. 20549

STATEMENT OF CHANGES IN BENEFICIAL OWNERSHIP

Filed pursuant to Section 16(a) of the Securities Exchange Act of 1934
or Section 30(h) of the Investment Company Act of 1940

OMB APPROVAL

OMB Number:			3235-0287
Estimated average burden
hours per response:			0.5

Check this box if no longer subject to Section 16. Form 4 or Form 5 obligations may continue. See Instruction 1(b).

Check this box to indicate that a transaction was made pursuant to a contract, instruction or written plan for the purchase or sale of equity securities of the issuer that is intended to satisfy the affirmative defense conditions of Rule 10b5-1(c). See Instruction 10.

1. Name and Address of Reporting Person^*

GALLAGHER JOHN R

(Last) (First) (Middle)

6100 4TH AVENUE S

SUITE 200

(Street)

SEATTLE WA 98108

(City) (State) (Zip)

2. Issuer Name and Ticker or Trading Symbol
TRUPANION, INC. [ TRUP ]

5. Relationship of Reporting Person(s) to Issuer
(Check all applicable)

	Director		10% Owner
X	Officer (give title below)		Other (specify below)
	Chief Operating Officer

3. Date of Earliest Transaction (Month/Day/Year)
11/24/2025

4. If Amendment, Date of Original Filed (Month/Day/Year)

6. Individual or Joint/Group Filing (Check Applicable Line)

X	Form filed by One Reporting Person
	Form filed by More than One Reporting Person

Table I - Non-Derivative Securities Acquired, Disposed of, or Beneficially Owned
1. Title of Security (Instr. 3)	2. Transaction Date (Month/Day/Year)	2A. Deemed Execution Date, if any (Month/Day/Year)	3. Transaction Code (Instr. 8)		4. Securities Acquired (A) or Disposed Of (D) (Instr. 3, 4 and 5)			5. Amount of Securities Beneficially Owned Following Reported Transaction(s) (Instr. 3 and 4)	6. Ownership Form: Direct (D) or Indirect (I) (Instr. 4)	7. Nature of Indirect Beneficial Ownership (Instr. 4)
			Code	V	Amount	(A) or (D)	Price
Common Stock	11/24/2025		M		3,328	A	(1)	35,712	D
Common Stock	11/24/2025		F		1,309(2)	D	$35.4	34,403	D
Common Stock	11/24/2025		M		2,570	A	(1)	36,973	D
Common Stock	11/24/2025		F		735(2)	D	$35.4	36,238	D
Common Stock	11/24/2025		M		3,460	A	(1)	39,698	D
Common Stock	11/24/2025		F		1,361(2)	D	$35.4	38,337	D

Table II - Derivative Securities Acquired, Disposed of, or Beneficially Owned (e.g., puts, calls, warrants, options, convertible securities)
1. Title of Derivative Security (Instr. 3)	2. Conversion or Exercise Price of Derivative Security	3. Transaction Date (Month/Day/Year)	3A. Deemed Execution Date, if any (Month/Day/Year)	4. Transaction Code (Instr. 8)		5. Number of Derivative Securities Acquired (A) or Disposed of (D) (Instr. 3, 4 and 5)		6. Date Exercisable and Expiration Date (Month/Day/Year)		7. Title and Amount of Securities Underlying Derivative Security (Instr. 3 and 4)		8. Price of Derivative Security (Instr. 5)	9. Number of derivative Securities Beneficially Owned Following Reported Transaction(s) (Instr. 4)	10. Ownership Form: Direct (D) or Indirect (I) (Instr. 4)	11. Nature of Indirect Beneficial Ownership (Instr. 4)
				Code	V	(A)	(D)	Date Exercisable	Expiration Date	Title	Amount or Number of Shares
Restricted Stock Unit (RSU)	(1)	11/24/2025		M			3,328	(3)	02/22/2027(3)	Common Stock	3,328	$0	16,637	D
Restricted Stock Unit (RSU)	(1)	11/24/2025		M			2,570	(4)	02/22/2026(4)	Common Stock	2,570	$0	2,570	D
Restricted Stock Unit (RSU)	(1)	11/24/2025		M			3,460	(5)	11/22/2028(5)	Common Stock	3,460	$0	10,378	D

Explanation of Responses:

1. Restricted stock units convert into common stock on a one-for-one basis.

2. 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.

3. 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.

4. 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.

5. 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.

Remarks:

	/s/ Christina Poler as attorney-in-fact for John R. Gallagher	11/25/2025
	** Signature of Reporting Person	Date
Reminder: Report on a separate line for each class of securities beneficially owned directly or indirectly.
* If the form is filed by more than one reporting person, see Instruction 4 (b)(v).
** Intentional misstatements or omissions of facts constitute Federal Criminal Violations See 18 U.S.C. 1001 and 15 U.S.C. 78ff(a).
Note: File three copies of this Form, one of which must be manually signed. If space is insufficient, see Instruction 6 for procedure.
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FAQ

What insider transaction did Trupanion (TRUP) disclose for its COO?

The filing reports that Chief Operating Officer John R. Gallagher had several restricted stock unit (RSU) awards convert into Trupanion common stock on November 24, 2025, with some shares withheld to cover taxes.

How many Trupanion (TRUP) shares does the COO own after the reported Form 4 transactions?

Following the reported RSU conversions and tax withholdings on November 24, 2025, John R. Gallagher directly owned 38,337 shares of Trupanion common stock.

Were any of the Trupanion (TRUP) shares reported on the Form 4 actually sold by the COO?

The filing explains that 1,309, 735, and 1,361 shares were withheld by the issuer at $35.4 per share to satisfy income tax withholding and remittance obligations and do not represent a sale by John R. Gallagher.

What RSU grants underlie the Trupanion (TRUP) Form 4 transactions for John R. Gallagher?

The transactions relate to prior RSU grants of 26,619 units on February 27, 2025, 20,559 units on February 27, 2024, and 13,838 units on November 12, 2024, each vesting over time subject to continued service.

How do Trupanion (TRUP) restricted stock units convert into common stock for the COO?

The filing states that restricted stock units convert into common stock on a one-for-one basis, meaning each vested RSU becomes one share of Trupanion common stock.

What was the tax withholding price used in the Trupanion (TRUP) Form 4 transactions?

For the shares withheld to cover income tax obligations on November 24, 2025, the issuer used a price of $35.4 per share.