[Form 4] Trupanion, Inc. Insider Trading Activity

Rhea-AI Filing Summary

Margaret Tooth, CEO and Director of Trupanion, Inc. (TRUP), reported multiple restricted stock unit (RSU) vesting events on 08/22/2025 that converted into common stock. The Form 4 shows the vesting/conversion of RSUs into shares in several tranches (12,170; 313; 6,250; 6,250), with the issuer withholding shares to satisfy tax withholding obligations (4,788; 123; 2,459; 2,459) at a disclosed withholding price of $46.63 per share. The document lists resulting beneficial ownership counts after each reported transaction (examples include 141,466; 136,678; 136,991; 136,868; 143,118; 140,659; 146,909; 144,450). The RSUs convert one-for-one into common stock and have differing vest schedules and future vesting dates noted in the filing.

Positive

• Executive alignment with shareholders: Multiple RSU vestings converted into common stock, increasing the CEO's equity stake and aligning interests with shareholders.
• Transparent tax treatment: The issuer withheld specified shares to satisfy tax withholding obligations, which is clearly disclosed and shows administrative compliance.

Negative

• Net share increase reduced by withholding: A material portion of vested shares were withheld (4,788; 123; 2,459; 2,459), lowering the immediate net uplift in outstanding shares held by the reporting person.

Insights

Financial Analyst

TL;DR: CEO received vested RSUs that increased her common shares while standard tax-withholding reduced the net share increase.

The filing documents routine executive compensation vesting rather than open-market purchases or sales. Multiple RSU tranches vested on 08/22/2025 converting into common stock one-for-one, increasing reported beneficial ownership in step changes. A portion of shares was withheld by the issuer to satisfy tax obligations at an indicated withholding rate equating to a $46.63 per-share withholding price for the disclosed withheld tranches. This is a typical mechanics-driven disclosure with no indication of market sales by the reporting person.

Corporate Governance Expert

TL;DR: The disclosure reflects standard equity compensation governance mechanics—scheduled RSU vesting and issuer tax withholding.

The Form 4 clearly attributes the increase in direct ownership to vesting RSUs granted on prior grant dates with specified future vest schedules. The filing confirms the company withheld shares to meet tax remittance obligations, an ordinary administrative action. There are no signs of unusual insider trading, accelerated dispositions, or changes to service-based vesting terms in this report.

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)
08/22/2025

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		12,170	A	(1)	141,466	D
Common Stock	08/22/2025		F		4,788(2)	D	$46.63	136,678	D
Common Stock	08/22/2025		M		313	A	(1)	136,991	D
Common Stock	08/22/2025		F		123(2)	D	$46.63	136,868	D
Common Stock	08/22/2025		M		6,250	A	(1)	143,118	D
Common Stock	08/22/2025		F		2,459(2)	D	$46.63	140,659	D
Common Stock	08/22/2025		M		6,250	A	(1)	146,909	D
Common Stock	08/22/2025		F		2,459(2)	D	$46.63	144,450	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			12,170	(3)	08/22/2028(3)	Common Stock	12,170	$0	36,509	D
Restricted Stock Unit (RSU)	(1)	08/22/2025		M			313	(4)	02/22/2028(4)	Common Stock	313	$0	3,125	D
Restricted Stock Unit (RSU)	(1)	08/22/2025		M			6,250	(5)	02/22/2027(5)	Common Stock	6,250	$0	37,500	D
Restricted Stock Unit (RSU)	(1)	08/22/2025		M			6,250	(6)	02/22/2026(6)	Common Stock	6,250	$0	12,500	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 19, 2024, the reporting person was granted 48,679 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 22, 2025, after which 1/16th of the total shares vest quarterly, subject to continued service through each vest date.

4. On February 27, 2024, the reporting person was granted 5,000 restricted stock units (RSUs). The RSUs vest and convert into common stock of the Issuer as to 1/4th of the total shares on February 22, 2025, after which 1/16th of the total shares vest quarterly, subject to continued service through each vest date.

5. On February 27, 2025, the reporting person was granted 50,000 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.

6. On February 27, 2024, the reporting person was granted 50,000 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 Margaret Tooth	08/26/2025
	** Signature of Reporting Person	Date
Reminder: Report on a separate line for each class of securities beneficially owned directly or indirectly.
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FAQ

Who filed the Form 4 for TRUP and what is their role?

The filing was made by Margaret Tooth, who is identified as both CEO and a Director of Trupanion, Inc.

What triggered the Form 4 reporting on 08/22/2025 for TRUP?

Vesting/conversion of restricted stock units (RSUs) into common stock occurred on 08/22/2025, prompting the Form 4 disclosure.

How many RSU shares converted into common stock on 08/22/2025?

Reported RSU conversions included 12,170; 313; 6,250; and 6,250 shares in separate tranches as shown in the filing.

Were any shares withheld to satisfy taxes and at what price?

Yes. The issuer withheld shares to satisfy income tax withholding: 4,788; 123; 2,459; and 2,459 shares, with a disclosed withholding price of $46.63 for the reported withheld tranches.

Do the RSUs convert one-for-one into common stock?

Yes. The filing states the RSUs convert into common stock on a one-for-one basis.

Are there future vesting schedules noted in the filing?

Yes. The filing references grant dates and vest schedules for the RSUs, including future vest dates and staggered vesting percentages for each grant.