[Form 4] TRUPANION, INC. Insider Trading Activity

Rhea-AI Filing Summary

Trupanion, Inc. (TRUP)11/24/2025, multiple restricted stock unit (RSU) awards vested and converted into common stock, including blocks of 312, 6,250, 3,042 and another 6,250 shares on a one-for-one basis. In connection with these vestings, the issuer withheld 122, 2,459, 1,197 and 2,459 shares at a price of $35.4 per share to cover tax obligations, which is reported as a disposition but not a sale by the insider. Following these transactions, Tooth directly beneficially owns 150,962 shares of Trupanion common stock and continues to hold several RSU awards that are scheduled to vest over future dates if service conditions are met.

11/25/2025 - 09:30 PM

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^*

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)
11/24/2025

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	11/24/2025		M		312	A	(1)	141,657	D
Common Stock	11/24/2025		F		122(2)	D	$35.4	141,535	D
Common Stock	11/24/2025		M		6,250	A	(1)	147,785	D
Common Stock	11/24/2025		F		2,459(2)	D	$35.4	145,326	D
Common Stock	11/24/2025		M		3,042	A	(1)	148,368	D
Common Stock	11/24/2025		F		1,197(2)	D	$35.4	147,171	D
Common Stock	11/24/2025		M		6,250	A	(1)	153,421	D
Common Stock	11/24/2025		F		2,459(2)	D	$35.4	150,962	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)	11/24/2025		M			312	(3)	02/22/2028(3)	Common Stock	312	$0	2,813	D
Restricted Stock Unit (RSU)	(1)	11/24/2025		M			6,250	(4)	02/22/2026(4)	Common Stock	6,250	$0	6,250	D
Restricted Stock Unit (RSU)	(1)	11/24/2025		M			3,042	(5)	08/22/2028(5)	Common Stock	3,042	$0	33,467	D
Restricted Stock Unit (RSU)	(1)	11/24/2025		M			6,250	(6)	02/22/2027(6)	Common Stock	6,250	$0	31,250	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 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.

4. 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.

5. 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.

6. 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.

Remarks:

	/s/ Christina Poler as attorney-in-fact for Margaret Tooth	11/25/2025
	** 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 did Trupanion (TRUP) disclose in this Form 4 filing?

The filing reports that CEO and director Margaret Tooth had several restricted stock unit (RSU) awards vest on 11/24/2025, converting into Trupanion common stock with related share withholding for taxes.

How many Trupanion (TRUP) shares does the insider now beneficially own?

After the reported transactions, Margaret Tooth directly beneficially owns 150,962 shares of Trupanion common stock.

What RSU awards are described for the Trupanion (TRUP) CEO in this filing?

The filing describes RSU grants of 5,000 units on February 27, 2024, 50,000 units on the same date, 48,679 units on August 19, 2024, and another 50,000 units on February 27, 2025, each vesting in tranches over time, subject to continued service.

Were any of the Trupanion (TRUP) insider transactions open-market sales?

No. The filing states that the reported dispositions labeled with code F represent shares withheld by the issuer to satisfy income tax withholding and remittance obligations and do not represent a sale by the reporting person.

At what price were Trupanion (TRUP) shares withheld for taxes in this Form 4?

Shares of Trupanion common stock were withheld at a price of $35.4 per share to cover tax obligations associated with RSU vesting.

How do the Trupanion (TRUP) RSUs convert into common stock for the CEO?

The filing explains that restricted stock units convert into common stock on a one-for-one basis, with each award vesting in scheduled fractions (such as 1/4 or 1/8 initially, then quarterly 1/16 or 1/8) contingent on continued service through each vest date.