TRUP CEO exercises 6,000 options, reports sales at ~$43.74

Q: What did TRUP’s CEO report on Form 4?

Margaret Tooth reported exercising 6,000 options at $8.93 and selling 6,000 shares at $43.7233 and 2,884 shares at $43.7424 on 10/27/2025 .

Q: Was the TRUP insider trade under a 10b5-1 plan?

Yes. The filing states the transactions were under a Rule 10b5-1 trading plan adopted on June 6, 2025 .

Q: How many TRUP shares does the insider hold after the trade?

After the reported transactions, Tooth directly beneficially owned 141,345 shares .

Q: How many stock options remain after the transactions?

The filing shows 16,000 stock options beneficially owned following the transactions.

Q: What were the sale price details for the TRUP shares?

The prices are weighted averages with trades executed in ranges of $43.4200–$44.0500 and $43.5700–$44.0500 .

Q: Is the reported option grant vested and when does it expire?

Yes, the stock option grant is fully vested and expires on 12/21/2025 .

Filing Impact

(High)

Filing Sentiment

(Negative)

Form Type

Rhea-AI Filing Summary

Trupanion, Inc. (TRUP) CEO and director Margaret Tooth reported a Rule 10b5-1(c) trade on 10/27/2025.

She exercised 6,000 options at $8.93 and then sold 6,000 shares at a weighted average price of $43.7233 and 2,884 shares at a weighted average price of $43.7424. The sales were executed in multiple transactions within stated price ranges under a pre‑arranged trading plan adopted on June 6, 2025.

Following these transactions, Tooth beneficially owned 141,345 shares of common stock directly and held 16,000 stock options outstanding. The referenced stock option grant is fully vested and expires on 12/21/2025.

Insider Trade Summary

Net Seller: 8,884 shares ($388,493)

Net Sell 4 txns

Insider Tooth Margaret

Role CEO

Sold 8,884 shs ($388K)

Type	Security	Shares	Price	Value
Exercise	Stock Option (right to buy)	6,000	$0.00	--
Exercise	Common Stock	6,000	$8.93	$54K
Sale	Common Stock	6,000	$43.7233	$262K
Sale	Common Stock	2,884	$43.7424	$126K

Holdings After Transaction: Stock Option (right to buy) — 16,000 shares (Direct); Common Stock — 150,229 shares (Direct)

Footnotes (1)

The exercise and sale reported were effected pursuant to a Rule 10b5-1 trading plan adopted by reporting person on June 6, 2025, in order to implement a plan of financial diversification. Accordingly, the reporting person had no discretion with regard to the timing of the transaction. The reported price in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $43.4200 to $44.0500 per share, inclusive. The reporting person undertakes to provide to the issuer, any security holder of the issuer, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the range set forth in this footnote (2). The reported price in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $43.5700 to $44.0500 per share, inclusive. The reporting person undertakes to provide to the issuer, any security holder of the issuer, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the range set forth in this footnote (3). This stock option grant is fully vested.

Form 4 Insider Transactions: What Each Field Means →

10/29/2025 - 07:04 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

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)
10/27/2025

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)
1. Title of Security (Instr. 3)	2. Transaction Date (Month/Day/Year)	2A. Deemed Execution Date, if any (Month/Day/Year)	Code	V	Amount	(A) or (D)	Price		6. Ownership Form: Direct (D) or Indirect (I) (Instr. 4)	7. Nature of Indirect Beneficial Ownership (Instr. 4)
Common Stock	10/27/2025		M⁽¹⁾		6,000	A	$8.93	150,229	D
Common Stock	10/27/2025		S⁽¹⁾		6,000	D	$43.7233⁽²⁾	144,229	D
Common Stock	10/27/2025		S⁽¹⁾		2,884	D	$43.7424⁽³⁾	141,345	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)
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)	Code	V	(A)	(D)	Date Exercisable	Expiration Date	Title	Amount or Number of Shares	8. Price of Derivative Security (Instr. 5)		10. Ownership Form: Direct (D) or Indirect (I) (Instr. 4)	11. Nature of Indirect Beneficial Ownership (Instr. 4)
Stock Option (right to buy)	$8.93	10/27/2025		M⁽¹⁾			6,000	⁽⁴⁾	12/21/2025	Common Stock	6,000	$0	16,000	D

Explanation of Responses:

1. The exercise and sale reported were effected pursuant to a Rule 10b5-1 trading plan adopted by reporting person on June 6, 2025, in order to implement a plan of financial diversification. Accordingly, the reporting person had no discretion with regard to the timing of the transaction.

2. The reported price in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $43.4200 to $44.0500 per share, inclusive. The reporting person undertakes to provide to the issuer, any security holder of the issuer, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the range set forth in this footnote (2).

3. The reported price in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $43.5700 to $44.0500 per share, inclusive. The reporting person undertakes to provide to the issuer, any security holder of the issuer, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the range set forth in this footnote (3).

4. This stock option grant is fully vested.

Remarks:

	/s/ Christina Poler as attorney-in-fact for Margaret Tooth	10/29/2025
	** 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.

Source: View Original Filing on SEC EDGAR

FAQ

What did TRUP’s CEO report on Form 4?

Margaret Tooth reported exercising 6,000 options at $8.93 and selling 6,000 shares at $43.7233 and 2,884 shares at $43.7424 on 10/27/2025.

Was the TRUP insider trade under a 10b5-1 plan?

Yes. The filing states the transactions were under a Rule 10b5-1 trading plan adopted on June 6, 2025.

How many TRUP shares does the insider hold after the trade?

After the reported transactions, Tooth directly beneficially owned 141,345 shares.

How many stock options remain after the transactions?

The filing shows 16,000 stock options beneficially owned following the transactions.

What were the sale price details for the TRUP shares?

The prices are weighted averages with trades executed in ranges of $43.4200–$44.0500 and $43.5700–$44.0500.

Is the reported option grant vested and when does it expire?

Yes, the stock option grant is fully vested and expires on 12/21/2025.