[Form 4] Trupanion, Inc. Insider Trading Activity

Rhea-AI Filing Summary

Simon Wheeler, EVP, Trupanion International, reported multiple transactions in Trupanion, Inc. (TRUP) related to the vesting and conversion of restricted stock units (RSUs) on 08/25/2025. The filing shows 974 RSUs vested and converted into 974 shares of common stock and 322 RSUs vested and converted into 322 shares. The report also discloses that the issuer withheld 457 shares and 151 shares to satisfy income tax withholding obligations in connection with the RSU vesting; these withheld shares are not sales by the reporting person. After the transactions, the reporting person beneficially owned 19,341 shares, then 18,884 shares, then 19,206 shares, and finally 19,055 shares as shown on separate reported lines reflecting each event and withholding. The Form 4 was signed by an attorney-in-fact on 08/27/2025.

Positive

• RSU vesting occurred as scheduled: 974 and 322 RSUs converted to common stock on 08/25/2025.
• Withholding disclosed as issuer action: 457 and 151 shares withheld to satisfy tax obligations, explicitly noted as not a sale by the reporting person.
• Grant history documented: Filing cites original RSU grants from 11/12/2021 (15,588 RSUs) and 08/14/2023 (5,144 RSUs) and their vesting schedules.

Negative

• None.

Insights

Securities Analyst

TL;DR: Routine executive compensation vesting: small RSU conversions and issuer tax-withholding disclosed; no open-market sale by the insider.

The Form 4 documents standard vesting-related activity rather than active trading. Specifically, 974 and 322 restricted stock units vested and converted to common shares on 08/25/2025. The issuer withheld 457 and 151 shares to satisfy tax withholding obligations; the filing explicitly states these withholdings do not represent sales by the reporting person. The sequence of reported beneficial ownership figures corresponds to the vesting and withholding events. For investors, this is a compensation-related disclosure that does not indicate voluntary disposition or acquisition beyond the conversion mechanics and tax remittance.

Corporate Governance Expert

TL;DR: Governance disclosure shows expected equity compensation mechanics; no governance or control change reported.

The disclosure confirms that RSUs granted in 2021 and 2023 are subject to scheduled vesting and conversion rules described in the explanations. The filing references the grant schedules: the 2021 grant (15,588 RSUs) and the 2023 grant (5,144 RSUs) with quarter-based vesting after initial cliff vesting, as stated. The transactions are administrative outcomes of those plans and the tax withholding process; there is no indication of any change in the reporting person’s role, control, or a material governance event in this filing.

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
Estimated average burden
hours per response:			0.5

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)
08/25/2025

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		974	A	(1)	19,341	D
Common Stock	08/25/2025		F		457(2)	D	$45.83	18,884	D
Common Stock	08/25/2025		M		322	A	(1)	19,206	D
Common Stock	08/25/2025		F		151(2)	D	$45.83	19,055	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			974	(3)	11/25/2025(3)	Common Stock	974	$0	975	D
Restricted Stock Unit (RSU)	(1)	08/25/2025		M			322	(4)	08/25/2027(4)	Common Stock	322	$0	2,572	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 November 12, 2021, the reporting person was granted 15,588 restricted stock units (RSUs). The RSUs vested and converted into common stock of the Issuer as to 1/4th of the total shares on November 25, 2022, after which 1/16th of the total shares vest quarterly, subject to continued service through each vest date.

4. On August 14, 2023, the reporting person was granted 5,144 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 Simon Wheeler	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.
Persons who respond to the collection of information contained in this form are not required to respond unless the form displays a currently valid OMB Number.

FAQ

What transactions did Simon Wheeler (EVP, Trupanion International) report on Form 4 for TRUP?

The Form 4 reports that on 08/25/2025 restricted stock units vested and converted into 974 and 322 shares of Trupanion common stock, with 457 and 151 shares withheld for tax withholding.

Were any of the withheld shares sales by the reporting person according to the filing?

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

How many shares did the reporting person beneficially own following the reported transactions?

The filing lists beneficial ownership figures on the reported lines as 19,341, 18,884, 19,206, and 19,055 shares following the respective reported events.

What RSU grant schedules does the Form 4 reference?

The filing references a 11/12/2021 grant of 15,588 RSUs with initial vesting on 11/25/2022 and subsequent quarterly vesting, and an 08/14/2023 grant of 5,144 RSUs with initial vesting on 08/25/2024 and subsequent quarterly vesting.

Who signed the Form 4 filing and when?

The Form 4 was signed by /s/ Christina Poler as attorney-in-fact for Simon Wheeler on 08/27/2025.