[Form 4] Trupanion, Inc. Insider Trading Activity

Rhea-AI Filing Summary

Trupanion, Inc. (TRUP) Form 4 summary: Brenna McGibney, Chief Administration Officer, reported multiple restricted stock unit (RSU) vesting-related transactions on 08/25/2025. Several RSU tranches converted into common stock on a one-for-one basis, with amounts reported as acquired (codes M) and shares withheld by the issuer to satisfy tax withholding (codes F) at a withheld price of $45.83 per share. Following the reported transactions, Ms. McGibney beneficially owns varying direct share totals across tranches (examples include 3,433, 3,417, 3,872, and 3,692 shares). The filing explains grant and vesting schedules for RSUs awarded in 2022 and 2023.

Positive

• RSU conversions are clearly documented and follow stated grant/vesting schedules, enhancing transparency
• Tax withholding shares are disclosed (code F at $45.83), showing compliance with employer remittance obligations

Negative

• No material open-market purchases were reported that would increase insider ownership beyond routine vesting

Insights

Financial Analyst

TL;DR Insider activity reflects routine RSU vesting with tax withholding; no open-market sales disclosed.

The reported activity consists primarily of RSU conversions into common stock and issuer withholding to cover tax obligations at $45.83 per share. These transactions are compensation-related rather than discretionary sales, indicating compensation realization rather than a change in investment stance. The magnitude of shares disclosed is modest relative to typical market capitalization considerations and appears routine given the documented grant schedules from 2022 and 2023.

Corporate Governance Expert

TL;DR Vesting-related disclosure is standard and consistent with grant terms; withholding noted for tax compliance.

The Form 4 provides clear disclosure of RSU vesting schedules, conversion mechanics (one-for-one), and issuer withholding for taxes. The filing includes grant dates and vesting patterns, supporting transparency on insider compensation realization. No indications of unusual accelerated vesting, discretionary sales, or change-in-control triggers are present in the disclosed text.

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^*

MCGIBNEY BRENNA

(Last) (First) (Middle)

309-1277 LYNN VALLEY ROAD

(Street)

NORTH VANCOUVER A1 V7J 0A2

(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)
	Chief Administration Officer

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		31	A	(1)	3,433	D
Common Stock	08/25/2025		F		16(2)	D	$45.83	3,417	D
Common Stock	08/25/2025		M		233	A	(1)	3,650	D
Common Stock	08/25/2025		F		124(2)	D	$45.83	3,526	D
Common Stock	08/25/2025		M		17	A	(1)	3,543	D
Common Stock	08/25/2025		F		9(2)	D	$45.83	3,534	D
Common Stock	08/25/2025		M		338	A	(1)	3,872	D
Common Stock	08/25/2025		F		180(2)	D	$45.83	3,692	D
Common Stock	08/25/2025		M		27	A	(1)	3,719	D
Common Stock	08/25/2025		F		14(2)	D	$45.83	3,705	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			31	(3)	02/27/2027(3)	Common Stock	31	$0	186	D
Restricted Stock Unit (RSU)	(1)	08/25/2025		M			233	(4)	08/25/2026(4)	Common Stock	233	$0	935	D
Restricted Stock Unit (RSU)	(1)	08/25/2025		M			17	(5)	05/25/2027(5)	Common Stock	17	$0	121	D
Restricted Stock Unit (RSU)	(1)	08/25/2025		M			338	(6)	08/25/2027(6)	Common Stock	338	$0	2,705	D
Restricted Stock Unit (RSU)	(1)	08/25/2025		M			27	(7)	08/14/2023(7)	Common Stock	27	$0	217	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, 2023, the reporting person was granted 495 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, 2024, after which 1/16th of the total shares vest quarterly, subject to continued service through each vest date.

4. On August 12, 2022, the reporting person was granted 3,738 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 August 25, 2023, after which 1/16th of the total shares vest quarterly, subject to continued service through each vest date.

5. On May 15, 2023, the reporting person was granted 277 restricted stock units (RSUs). The RSUs vested and converted into common stock of the Issuer as to 1/4th of the total shares on May 25, 2024, after which 1/16th of the total shares vest quarterly, subject to continued service through each vest date.

6. On August 14, 2023, the reporting person was granted 5,410 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.

7. On August 14, 2023, the reporting person was granted 434 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 Brenna McGibney	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).
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FAQ

What did Brenna McGibney report on the Form 4 for TRUP?

The filing reports multiple RSU vesting conversions into common stock on 08/25/2025 and issuer withholding of shares for taxes at $45.83 per share.

Were any shares sold on the open market by the reporting person?

No open-market sales are disclosed; transactions labeled F reflect shares withheld by the issuer to satisfy tax withholding, not sales by the reporting person.

How many shares were involved in the reported transactions?

The Form 4 lists multiple tranche amounts; examples include conversions or holdings of 31, 233, 338, and tranche beneficial ownership totals such as 3,872 and 3,692 shares following transactions.

What grant and vesting history is documented in the filing?

The filing references RSU grants from February 27, 2023, August 12, 2022, May 15, 2023, and August 14, 2023, each with specified quarterly vesting schedules and initial 1/4th vest dates.

Does the Form 4 indicate any change in Ms. McGibney’s role or control status?

No; the form lists her as Chief Administration Officer and indicates direct beneficial ownership. There is no disclosure of role change or 10% ownership status.