[Form 4] Trupanion, Inc. Insider Trading Activity

Rhea-AI Filing Summary

Margaret Tooth, who is listed as both CEO and a Director of Trupanion, Inc. (TRUP), reported equity activity on Form 4 reflecting the vesting and conversion of restricted stock units into common stock on 08/25/2025. Two RSU groups converted into shares: 1,250 RSUs from a 2023 grant and 3,265 RSUs from a 2022 grant, adding stock to her direct holdings. The issuer withheld 491 and 1,284 shares, respectively, to satisfy tax withholding at a reported price of $45.83 per share; these withholdings are disclosures of remittance, not open-market sales. Beneficial ownership reported changed from 145,700 to 147,190 shares following the transactions. The form was signed by an attorney-in-fact on 08/27/2025.

Positive

• Vesting increased direct ownership: Scheduled RSU conversions added 4,515 underlying shares to the reporting person’s holdings before withholding adjustments.
• Withholding handled by issuer: Shares were withheld to satisfy tax obligations, indicating the transactions were compensation-related, not open-market sales.

Negative

• Net shares reduced by withholding: The issuer withheld a total of 1,775 shares for taxes, lowering the net shares delivered to the reporting person.
• No indication of cash purchase: All reported acquisitions are from RSU vesting; there are no reported purchases that would increase new capital investment by the insider.

Insights

Securities Analyst

TL;DR: Routine executive RSU vesting increased direct holdings; tax withholding reduced net received shares but did not indicate open-market selling.

The reported transactions are consistent with scheduled vesting of previously granted restricted stock units rather than discretionary sales or purchases. The issuer withheld 491 and 1,284 shares to satisfy tax obligations at the disclosed $45.83 withholding price, which reduces the net shares delivered to the reporting person but leaves overall beneficial ownership modestly higher after vesting. No cash sales or option exercises are reported. For investors, this is a standard insider vesting disclosure rather than a material change in control or capital structure.

Corporate Governance Expert

TL;DR: Disclosure shows compliance with Section 16 reporting and normal compensation mechanics; no red flags for governance practice.

The Form 4 documents expected conversion of RSUs granted in 2022 and 2023 under the company’s equity compensation arrangements. Withholding to cover taxes was executed by the issuer, as disclosed, and the filing was executed by an attorney-in-fact, which is an accepted administrative practice. There is no indication of abnormal timing, related-party transactions, or departures from standard award vesting schedules in the filing text provided.

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^*

Tooth Margaret

(Last) (First) (Middle)

C/O TRUPANION, INC.

6100 4TH AVENUE SOUTH, 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)

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

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		1,250	A	(1)	145,700	D
Common Stock	08/25/2025		F		491(2)	D	$45.83	145,209	D
Common Stock	08/25/2025		M		3,265	A	(1)	148,474	D
Common Stock	08/25/2025		F		1,284(2)	D	$45.83	147,190	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			1,250	(3)	08/25/2027(3)	Common Stock	1,250	$0	10,000	D
Restricted Stock Unit (RSU)	(1)	08/25/2025		M			3,265	(4)	02/25/2026(4)	Common Stock	3,265	$0	6,532	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 August 14, 2023, the reporting person was granted 20,000 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.

4. On February 28, 2022, the Reporting Person was granted 52,250 restricted stock units (RSUs). The RSUs vest and will convert to 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.

Remarks:

	/s/ Christina Poler as attorney-in-fact for Margaret Tooth	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).
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FAQ

Who reported the Form 4 for TRUP and what are their roles?

The reporting person is Margaret Tooth, identified as both CEO and a Director of Trupanion, Inc.

What equity transactions were reported on 08/25/2025 for TRUP?

Two RSU conversions into common stock were reported: 1,250 shares and 3,265 shares vested and converted on 08/25/2025.

Were any shares sold in these transactions for TRUP (TRUP)?

No open-market sales were reported. The filings show shares withheld by the issuer (491 and 1,284) to satisfy tax withholding, not sales.

What withholding details are disclosed on the Form 4?

The issuer withheld 491 and 1,284 shares to satisfy income tax withholding at a disclosed withholding price of $45.83 per share.

How did the reported transactions affect beneficial ownership?

Beneficial ownership figures reported moved from 145,700 to 147,190 shares after the vesting and withholding adjustments.