[Form 4] Trupanion, Inc. Insider Trading Activity

Rhea-AI Filing Summary

Insider vesting and tax withholding recorded for Trupanion, Inc. (TRUP). Steve Weinrauch, an executive (EVP, North America & Vet Strategy), had restricted stock units (RSUs) vest on 08/22/2025 that converted into common stock. The filing shows two vesting events: 2,932 RSUs from a 2025 grant and 2,028 RSUs from a 2024 grant converted to common shares. The report discloses that the issuer withheld 713 and 493 shares, respectively, to satisfy income tax withholding obligations, so the net beneficial ownership changed accordingly. Following the transactions, Weinrauch beneficially owned 17,590 shares attributable to the 2025 grant and 4,058 shares attributable to the 2024 grant, with total reported common shares held directly at the listed amounts.

Insights

Corporate Governance Expert

TL;DR: Routine RSU vesting with tax-withholding share retention; immaterial to company capital structure.

This Form 4 documents standard equity compensation mechanics: time-based RSU vesting and issuer share withholding for tax remittance. The transactions are grants from prior award dates (02/27/2024 and 02/27/2025) and reflect conversion one-for-one into common stock. No open-market sales or purchases were executed by the reporting person; withheld shares were retained by the issuer to meet tax obligations, not sold on the market. The filing contains no indication of a change in control, new grants beyond previously disclosed awards, or derivative exercises altering dilution beyond the planned vesting.

Compensation & Equity Plan Analyst

TL;DR: Compensation plan functioning as designed; vesting schedule and withholding executed per prior grants.

The disclosed vesting cadence (1/8th initial cliff then quarterly 1/8th) matches the explanatory notes tied to February grant dates. The number of RSUs vesting (2,932 and 2,028) and resulting beneficial ownership counts align with conversion mechanics. Withheld shares (713 and 493) represent customary tax-withholding practice upon vesting and are explicitly stated to be issuer-held for tax remittance, not market dispositions by the insider. No additional cashless exercises or non-standard transactions are reported.

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^*

WEINRAUCH STEVE

(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)
	EVP, North Am & Vet Strategy

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		2,932	A	(1)	62,389	D
Common Stock	08/22/2025		F		713(2)	D	$46.63	61,676	D
Common Stock	08/22/2025		M		2,028	A	(1)	63,704	D
Common Stock	08/22/2025		F		493(2)	D	$46.63	63,211	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			2,932	(3)	02/22/2027(3)	Common Stock	2,932	$0	17,590	D
Restricted Stock Unit (RSU)	(1)	08/22/2025		M			2,028	(4)	02/22/2026(4)	Common Stock	2,028	$0	4,058	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 23,453 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 16,229 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 Steve Weinrauch	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).
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 Steve Weinrauch report on Form 4 for TRUP?

The Form 4 reports vesting of RSUs on 08/22/2025 converting 2,932 and 2,028 RSUs into common stock, with share withholding for taxes.

How many shares were withheld for taxes in these transactions?

The issuer withheld 713 shares related to the 2025 grant and 493 shares related to the 2024 grant to satisfy income tax withholding.

Do these entries show insider open-market sales or purchases?

No. The filing shows RSU vesting and issuer withholding; it does not disclose any open-market sale or purchase by the reporting person.

What are the underlying grant dates referenced in the Form 4?

The explanatory notes state the RSUs were granted on February 27, 2025 (23,453 RSUs) and February 27, 2024 (16,229 RSUs), with the vesting schedule described in the filing.

How many shares does the filing show as beneficially owned after the transactions?

The filing reports 17,590 shares related to the 2025 grant and 4,058 shares related to the 2024 grant as beneficially owned following the transactions.