[Form 4] Trupanion, Inc. Insider Trading Activity

Rhea-AI Filing Summary

Simon Wheeler, Executive Vice President, Trupanion International, reported transactions on 08/22/2025 relating to the vesting of restricted stock units (RSUs) granted in 2024 and 2025. Several RSU vesting events converted units into common stock, resulting in multiple acquisitions of shares (totaling 2,991 shares acquired on that date across three vesting tranches) and contemporaneous withholding by the issuer to satisfy tax obligations (total withheld: 1,404 shares disposed at $46.63 per share). After these transactions, the reporting person beneficially owned between 17,278 and 18,804 shares across the reported lines depending on the line item. The filing notes the RSUs convert one-for-one to common stock and describes original grant schedules and vesting mechanics.

Insights

Corporate Compensation Analyst

TL;DR: Routine RSU vesting and tax withholding; increases vested stake but not a sale by the insider.

The Form 4 documents scheduled vesting of previously granted RSUs and issuer withholding to cover taxes. These are service-based, time-vesting awards from 2024 and 2025 grants converting one-for-one to common shares. The transactions reported as acquisitions (codes M) reflect conversion of RSUs into common stock; the reported dispositions (code F) are share withholdings by the issuer at $46.63 per share to satisfy tax obligations, not open-market sales by the reporting person. This is a routine compensation event with limited informational content about company performance.

Securities Compliance Specialist

TL;DR: Compliance filing appears complete and consistent with Rule 16 reporting for RSU vesting and tax withholding.

The filing lists transaction codes, amounts, and resulting beneficial ownership and includes explanatory notes describing grant dates, vesting schedules, and the issuer's withholding for taxes. Signature is provided via attorney-in-fact. The entries differentiate acquisitions from issuer withholding, aligning with disclosure norms. No indications of open-market sales or unusual related-party transactions are present.

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^*

WHEELER SIMON

(Last) (First) (Middle)

4TH FLOOR CHARTER HOUSE

WOODLANDS ROAD

(Street)

ALTRINCHAM X0 WA14 1HF

(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)
	EVP, Trupanion International

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		938	A	(1)	17,718	D
Common Stock	08/22/2025		F		440(2)	D	$46.63	17,278	D
Common Stock	08/22/2025		M		1,526	A	(1)	18,804	D
Common Stock	08/22/2025		F		717(2)	D	$46.63	18,087	D
Common Stock	08/22/2025		M		527	A	(1)	18,614	D
Common Stock	08/22/2025		F		247(2)	D	$46.63	18,367	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			938	(3)	02/25/2028(3)	Common Stock	938	$0	9,375	D
Restricted Stock Unit (RSU)	(1)	08/22/2025		M			1,526	(4)	02/22/2026(4)	Common Stock	1,526	$0	3,051	D
Restricted Stock Unit (RSU)	(1)	08/22/2025		M			527	(5)	02/22/2027(5)	Common Stock	527	$0	3,165	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, 2024, the reporting person was granted 15,000 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 25, 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 12,203 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 February 27, 2025, the reporting person was granted 4,219 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.

Remarks:

	/s/ Christina Poler as attorney-in-fact for Simon Wheeler	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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