[Form 4] TRUPANION, INC. Insider Trading Activity

Rhea-AI Filing Summary

Trupanion, Inc. (TRUP) director reports RSU conversions into common stock. On 11/24/2025, the reporting person acquired 312 shares of common stock and later 6,250 shares, following the exercise (code M) of restricted stock units (RSUs). After these transactions, the person directly beneficially owned 27,527 shares after the first acquisition and 33,777 shares after the second.

The transactions relate to RSU awards granted on February 27, 2024. One grant of 5,000 RSUs vests 1/4 of the shares on February 22, 2025, then 1/16 quarterly, while a separate grant of 50,000 RSUs vests 1/8 on May 22, 2024, then 1/8 quarterly, in each case subject to continued service. Following the reported activity, 2,813 RSUs remain from the smaller grant and 6,250 RSUs remain from the larger grant, each convertible into common stock on a one-for-one basis.

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

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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^*

RAWLINGS DARRYL

(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
	Officer (give title below)		Other (specify below)

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)	27,527	D
Common Stock	11/24/2025		M		6,250	A	(1)	33,777	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	(2)	02/22/2028(2)	Common Stock	312	$0	2,813	D
Restricted Stock Unit (RSU)	(1)	11/24/2025		M			6,250	(3)	02/22/2026(3)	Common Stock	6,250	$0	6,250	D

Explanation of Responses:

1. Restricted stock units convert into common stock on a one-for-one basis.

2. 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.

3. 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 Darryl Rawlings	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 insider transaction did Trupanion (TRUP) report on this Form 4?

The filing reports that a director of Trupanion, Inc. exercised restricted stock units (transaction code M) on 11/24/2025, acquiring 312 shares of common stock in one transaction and 6,250 shares in another.

How many Trupanion (TRUP) shares does the reporting person own after the Form 4 transactions?

After the reported transactions, the director directly beneficially owned 27,527 shares of common stock following the first acquisition and 33,777 shares following the second.

What RSU grants are described for the Trupanion (TRUP) director in this Form 4?

The Form 4 describes two RSU grants made on February 27, 2024: one for 5,000 RSUs and another for 50,000 RSUs, each converting into common stock on a one-for-one basis.

What are the vesting schedules for the Trupanion (TRUP) RSU awards?

The 5,000-unit RSU grant vests 1/4 of the shares on February 22, 2025, then 1/16 quarterly. The 50,000-unit grant vests 1/8 on May 22, 2024, then 1/8 quarterly, in each case subject to continued service.

How many Trupanion (TRUP) RSUs remain outstanding for the reporting person after these transactions?

After the reported exercises, the director beneficially owned 2,813 RSUs from the 5,000-unit grant and 6,250 RSUs from the 50,000-unit grant, each representing the right to receive the same number of common shares.

What is the role of the reporting person at Trupanion (TRUP)?

The reporting person is identified as a director of Trupanion, Inc. on this Form 4.