[Form 4] Trupanion, Inc. Insider Trading Activity

Rhea-AI Filing Summary

Darryl Rawlings, a director of Trupanion, Inc. (TRUP), reported multiple restricted stock unit (RSU) vesting events and transfers that changed his beneficial ownership. The Form 4 shows RSU conversions on 05/22/2025, 08/22/2025 and 08/25/2025 resulting in multiple small issuances of common stock and underlying RSU holdings tied to prior grants. The filing states a transfer of 634,172 shares to a limited liability company wholly owned by the reporting person and spouse, and reports indirect beneficial ownership of 1,463,281 shares via Kuyashii Primary Equities LLC. The form was signed by an attorney-in-fact on 08/27/2025.

Positive

• Updated beneficial ownership disclosed, showing 1,463,281 shares indirectly held via Kuyashii Primary Equities LLC
• RSU vesting schedules and conversion mechanics are explicitly disclosed for grants from 2022 and 2024, improving transparency

Negative

• Transfer of 634,172 shares to a limited liability company wholly owned by the reporting person and spouse is disclosed, changing direct ownership composition
• No cash exercise or sale details provided for these transactions beyond RSU conversions, limiting insight into liquidity or intent

Insights

Financial Analyst

TL;DR: Director converted RSUs and moved a large block into a wholly-owned LLC; ownership disclosure updated but results appear routine.

The reported activity reflects scheduled RSU vesting from grants in 2022 and 2024 and contemporaneous conversions into common stock on specified dates in May and August 2025. The filing discloses an indirect beneficial holding of 1,463,281 shares through Kuyashii Primary Equities LLC and documents a transfer of 634,172 shares to a wholly-owned limited liability company. These are disclosure and ownership-structure actions rather than operational results; they update outstanding insider holdings used in capitalization calculations.

Corporate Governance Expert

TL;DR: Insider disclosed routine vesting and a material intra-family transfer to an LLC; governance disclosure appears complete and timely.

The Form 4 identifies vesting mechanics tied to earlier RSU grants with vest dates and vesting schedules explicitly described. The filing also clarifies the nature of indirect ownership by naming the LLC and quantifying the transferred amount (634,172 shares). The form includes an attorney-in-fact signature dated 08/27/2025, fulfilling filing formalities. No departures, option exercises for cash, or other unusual governance events 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

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^*

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)
05/22/2025

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	05/22/2025		M		6,250	A	(1)	650,621	D
Common Stock	05/22/2025		M		312	A	(1)	650,933	D
Common Stock	05/22/2025		M		945	A	(1)	651,878	D
Common Stock	08/22/2025		M		6,250	A	(1)	23,956(2)	D
Common Stock	08/22/2025		M		313	A	(1)	24,269	D
Common Stock	08/25/2025		M		946	A	(1)	25,215	D
Common Stock								1,463,281(3)	I	By Kuyashii Primary Equities LLC

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)	05/22/2025		M			6,250	(4)	02/22/2026(4)	Common Stock	6,250	$0	18,750	D
Restricted Stock Unit (RSU)	(1)	05/22/2025		M			312	(5)	02/22/2028(5)	Common Stock	312	$0	3,438	D
Restricted Stock Unit (RSU)	(1)	05/22/2025		M			945	(6)	02/25/2026(6)	Common Stock	945	$0	2,838	D
Restricted Stock Unit (RSU)	(1)	08/22/2025		M			6,250	(4)	02/22/2026(4)	Common Stock	6,250	$0	12,500	D
Restricted Stock Unit (RSU)	(1)	08/22/2025		M			313	(5)	02/22/2028(5)	Common Stock	313	$0	3,125	D
Restricted Stock Unit (RSU)	(1)	08/25/2025		M			946	(6)	02/25/2026(6)	Common Stock	946	$0	1,892	D

Explanation of Responses:

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

2. Gives effect to transfer of 634,172 shares to a limited liability company, indirectly, wholly-owned by the reporting person and reporting person's spouse.

3. Includes shares described in Footnote (2).

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 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.

6. On February 28, 2022, the Reporting Person was granted 15,132 restricted stock units (RSUs). The RSUs vest and will convert to common stock of the Issuer as to 1/4th of the total shares on February 25, 2023, 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 Darryl Rawlings	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

Who filed the Form 4 for TRUP?

Darryl Rawlings, a director of Trupanion, Inc., filed the Form 4 (signed by an attorney-in-fact on 08/27/2025).

How many shares does Darryl Rawlings beneficially own after these transactions?

Indirect beneficial ownership of 1,463,281 shares is reported via Kuyashii Primary Equities LLC; direct holdings are listed separately in the filing.

What material transfer is reported on this Form 4?

The filing gives effect to a transfer of 634,172 shares to a limited liability company indirectly wholly-owned by the reporting person and the reporting person’s spouse.

What types of securities were reported on the Form 4?

The Form 4 reports Common Stock issuances from RSU conversions and Restricted Stock Units (RSUs) with specified vesting and conversion dates.

When did the relevant RSU conversions occur?

Reported RSU-related transactions occurred on 05/22/2025, 08/22/2025, and 08/25/2025.

Are the RSU grant dates and vesting schedules disclosed?

Yes. Grants from 02/27/2024 and 02/28/2022 are described with specific vesting schedules and subsequent quarterly vesting mechanics.