[Form 4] Trupanion, Inc. Insider Trading Activity

Rhea-AI Filing Summary

John R. Gallagher, Chief Operating Officer and director of Trupanion, Inc. (TRUP), reported RSU vesting and related share withholding on 08/22/2025. The filing shows the conversion/vesting of 3,327 and 2,570 restricted stock units into common stock, increasing his direct common stock holdings to 32,053 and 31,428 shares on two reported lines respectively. The company withheld 810 and 625 shares to satisfy income tax withholding obligations at an indicated price of $46.63 per share; those withheld shares are disclosed as dispositions and do not represent open-market sales. The RSUs originate from grants dated February 27, 2025 (26,619 RSUs) and February 27, 2024 (20,559 RSUs) with standard multi-quarter vesting schedules.

Positive

• Scheduled RSU vesting occurred, increasing the reporting person’s direct equity stake as intended by compensation plan.
• Withheld shares were used for tax remittance rather than open-market sales, indicating retention of most vested equity.

Negative

• Share withholding reduced net delivered shares (810 and 625 shares withheld), lowering the immediate increase in beneficial ownership.

Insights

Corporate Governance Expert

TL;DR: Executive received scheduled RSU vesting; withheld shares used for taxes, showing routine compensation mechanics and continued equity alignment.

The Form 4 documents routine vesting of previously granted restricted stock units for the COO and director. The withholding of 810 and 625 shares to satisfy tax obligations is explicitly disclosed and recorded as dispositions at $46.63 per share, which is standard practice and not a market sale. The remaining resulting direct ownership levels are reported. This filing contains no indications of unusual insider selling or change in control arrangements; it reflects scheduled compensation vesting consistent with the grant and vest schedules provided.

Executive Compensation Analyst

TL;DR: Vesting from 2024 and 2025 RSU grants was executed per schedule; tax withholding reduced net share delivery but preserves overall equity incentives.

The report ties vested RSUs to the February 27, 2024 and February 27, 2025 grants with defined 1/8th initial vesting and quarterly vesting thereafter. The disclosure clarifies that withheld shares are for tax remittance and not sales, preserving the intended retention and alignment purpose of RSU awards. The exercise/vesting dates and resulting share counts are clearly shown, enabling calculation of net share increases versus gross vesting amounts.

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
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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)
08/22/2025

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	08/22/2025		M		3,327	A	(1)	30,293	D
Common Stock	08/22/2025		F		810(2)	D	$46.63	29,483	D
Common Stock	08/22/2025		M		2,570	A	(1)	32,053	D
Common Stock	08/22/2025		F		625(2)	D	$46.63	31,428	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)	08/22/2025		M			3,327	(3)	02/22/2027(3)	Common Stock	3,327	$0	19,965	D
Restricted Stock Unit (RSU)	(1)	08/22/2025		M			2,570	(4)	02/22/2026(4)	Common Stock	2,570	$0	5,140	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.

Remarks:

	/s/ Christina Poler as attorney-in-fact for John R. Gallagher	08/26/2025
	** 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).
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FAQ

What transactions did John R. Gallagher report on Form 4 for TRUP?

He reported RSU vesting and related share withholding on 08/22/2025, including conversion of 3,327 and 2,570 RSUs and withholding of 810 and 625 shares for taxes.

Were any shares sold open-market by the reporting person in this filing?

No. The filing discloses shares withheld to satisfy tax obligations, which are recorded as dispositions, and explicitly notes these do not represent sales by the reporting person.

What price is shown for the withheld shares in the Form 4?

The withheld shares are reported at a price of $46.63 per share.

From which grant dates did the vested RSUs originate?

The vested RSUs originate from grants dated February 27, 2025 (26,619 RSUs) and February 27, 2024 (20,559 RSUs).

How do the RSU awards vest according to the filing?

The RSUs vest 1/8th on the initial vest date (May 22 of the grant year) and then 1/8th quarterly thereafter, subject to continued service.