[Form 4] Trupanion, Inc. Insider Trading Activity

Rhea-AI Filing Summary

John R. Gallagher, Chief Operating Officer of Trupanion, Inc. (TRUP), reported multiple restricted stock unit vesting events on 08/25/2025 that converted into common stock. The filings show a sequence of vesting (reported as "M" transactions) totaling newly issued shares and corresponding withholding by the issuer to satisfy tax obligations (reported as "F" transactions at $45.83 per share). The reporting table lists a final beneficial ownership of 32,384 shares of common stock following the transactions. Several RSU grants from 2022 and 2023 are described and vest according to their original schedules; some portions remain subject to future vesting dates through 2027.

Positive

• RSU vesting converted to common stock on 08/25/2025, increasing the reporting person’s direct ownership to 32,384 shares
• Withholding disclosed for tax obligations is explicitly identified and stated not to represent a sale by the reporting person
• Vesting schedules from grants in 2022 and 2023 are consistent with previously disclosed award terms through 2027

Negative

• None.

Insights

Financial Analyst

TL;DR: Executive RSUs vested and converted to 32,384 common shares; withholding occurred to satisfy taxes.

The Form 4 discloses ordinary-course compensation activity rather than an open-market sale or strategic transaction. Multiple RSU vesting events on 08/25/2025 increased Mr. Gallagher's direct holdings to 32,384 shares. The filing also shows withholding of a small number of shares at $45.83 per share to satisfy tax obligations; the filing explicitly states this withholding is not a sale by the reporting person. These movements are consistent with scheduled equity compensation vesting from grants made in 2022 and 2023 and do not in themselves indicate a change in corporate control or material financing activity.

Corporate Governance Expert

TL;DR: Reported vesting aligns executive incentives with shareholders; withholding to cover taxes is routine.

The disclosure documents routine equity compensation administration: RSUs granted in 2022 and 2023 vest per their stated schedules, some converted to common stock on 08/25/2025, and the issuer withheld shares to meet tax remittance obligations. Signature and attorney-in-fact execution are present and the report indicates individual filing by one reporting person. There are no indications of off-cycle discretionary awards, unusual derivative transactions, or related-party transfers in this Form 4.

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

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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)
08/25/2025

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	08/25/2025		M		28	A	(1)	31,456	D
Common Stock	08/25/2025		F		6(2)	D	$45.83	31,450	D
Common Stock	08/25/2025		M		735	A	(1)	32,185	D
Common Stock	08/25/2025		F		178(2)	D	$45.83	32,007	D
Common Stock	08/25/2025		M		451	A	(1)	32,458	D
Common Stock	08/25/2025		F		109(2)	D	$45.83	32,349	D
Common Stock	08/25/2025		M		45	A	(1)	32,394	D
Common Stock	08/25/2025		F		10(2)	D	$45.83	32,384	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)	08/25/2025		M			28	(3)	05/25/2027(3)	Common Stock	28	$0	202	D
Restricted Stock Unit (RSU)	(4)	08/25/2025		M			735	(5)	02/25/2026(5)	Common Stock	735	$0	1,469	D
Restricted Stock Unit (RSU)	(4)	08/25/2025		M			451	(6)	08/25/2027(6)	Common Stock	451	$0	3,612	D
Restricted Stock Unit (RSU)	(4)	08/25/2025		M			45	(7)	08/25/2027(7)	Common Stock	45	$0	360	D

Explanation of Responses:

1. The RSUs 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 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.

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

5. 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.

6. 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.

7. 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.

Remarks:

	/s/ Christina Poler as attorney-in-fact for John R. Gallagher	08/27/2025
	** 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 transactions did John R. Gallagher report on Form 4 for TRUP?

The Form 4 reports RSU vesting events on 08/25/2025 that converted into common stock and shows share withholding by the issuer to satisfy tax obligations at $45.83 per share.

How many TRUP shares does John R. Gallagher beneficially own after the reported transactions?

Following the reported transactions, the filing shows Mr. Gallagher beneficially owns 32,384 shares of common stock.

Were any shares sold by the reporting person in these transactions for TRUP?

No. The filing states the shares withheld were by the issuer to satisfy income tax withholding and do not represent a sale by the reporting person.

Which RSU grants are referenced in the Form 4 for TRUP?

The Form 4 references RSU grants dated February 28, 2022, May 15, 2023, and August 14, 2023, with vesting schedules described in the filing.

Who signed the Form 4 for John R. Gallagher (TRUP)?

The Form 4 is signed by Christina Poler as attorney-in-fact for John R. Gallagher dated 08/27/2025.