Trupanion director gains 312 shares via RSU vest

Trupanion director Darryl Rawlings exercised restricted stock units into common shares.

Rhea-AI Filing Summary

Trupanion director Darryl Rawlings exercised restricted stock units into common shares. On May 22, 2026, 312 RSUs converted into 312 shares of common stock, reflecting a one-for-one conversion ratio. Following this exercise, Rawlings directly held 24,838 common shares and 2,188 RSUs.

A footnote explains that his reported beneficial ownership has been adjusted to correct two scrivener's errors in prior Form 4 filings, reattributing a previously reported 20,700-share purchase to indirect beneficial owner Kuyashii Primary Equities LLC and removing 2,994 shares that had been reported as tax withholdings.

Insider Trade Summary

312 shares exercised/converted

Exercise 2 txns

Insider RAWLINGS DARRYL

Role Director

Type	Security	Shares	Price	Value
Exercise	Restricted Stock Unit (RSU)	312	$0.00	$0.00
Exercise	Common Stock	312	$0.00	$0.00

Holdings After Transaction: Restricted Stock Unit (RSU) — 2,188 contracts (Direct); Common Stock — 24,838 shares (Direct)

Footnotes (3)

1. F1. Restricted stock units convert into common stock on a one-for-one basis.
2. F2. The total amount of securities beneficially owned by the reporting person has been adjusted to correct two (2) scrivener's errors. (1) On May 7, 2024, a Form 4 was filed reporting a direct purchase of 20,700 shares by the reporting person; however, such shares were in fact purchased by indirect beneficial owner Kuyashii Primary Equities LLC; and (2) Form 4s were filed on February 26, 2025 and on February 27, 2025 to report tax withholdings in the aggregate amount of 2,994 shares, however there was no tax withholdings at that time because the reporting person was no longer providing services as an employee. The total number of securities beneficially owned and as reported in Table I has been adjusted accordingly to reflect the reporting person's current beneficial ownership as of the transaction date.
3. F3. 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.

Key Figures

RSUs exercised: 312 shares Common shares held after: 24,838 shares RSUs held after: 2,188 units +3 more

6 metrics

RSUs exercised 312 shares RSUs converted into common stock on May 22, 2026

Common shares held after 24,838 shares Direct Trupanion common stock holdings after transaction

RSUs held after 2,188 units Remaining restricted stock units following the 312-unit conversion

Original RSU grant 5,000 units RSUs granted on February 27, 2024 with staged vesting

Reattributed share purchase 20,700 shares Previously reported as direct; attributed to Kuyashii Primary Equities LLC

Corrected tax withholding total 2,994 shares Previously reported as tax withholdings; removed in ownership adjustment

Key Terms

Restricted stock units, scrivener's errors, indirect beneficial owner, beneficially owned, +1 more

5 terms

Restricted stock units financial

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

Restricted stock units are a type of company reward where employees are promised shares of stock, but they only fully own these shares after meeting certain conditions, like staying with the company for a set time. They matter because they can become valuable assets and are often used to motivate employees to help the company succeed.

scrivener's errors financial

"adjusted to correct two (2) scrivener's errors."

indirect beneficial owner financial

"shares were in fact purchased by indirect beneficial owner Kuyashii Primary Equities LLC"

beneficially owned financial

"The total amount of securities beneficially owned by the reporting person has been adjusted"

Beneficially owned describes securities or assets where a person has the economic rights and control—such as the right to receive dividends and to direct voting—even if legal title is held in another name. Think of it like having the keys and using a car that’s registered to someone else: you get the benefits and make decisions. Investors care because beneficial ownership reveals who truly controls value and voting power, affecting corporate decisions and takeover dynamics.

vest quarterly financial

"after which 1/16th of the total shares vest quarterly, subject to continued service"

AI-generated analysis. How Rhea-AI works. Not financial advice.

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Accepted by SEC EDGAR 05/27/2026 - 09:57 PM EDT Learn about SEC filing dates

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 WASHINGTON 98108

(City) (State) (Zip)

UNITED STATES

(Country)

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)

2a. Foreign Trading Symbol

3. Date of Earliest Transaction (Month/Day/Year)
05/22/2026

6. Individual or Joint/Group Filing (Check Applicable Line)

X	Form filed by One Reporting Person
	Form filed by More than One Reporting Person

4. If Amendment, Date of Original Filed (Month/Day/Year)

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	05/22/2026		M		312	A	(1)	24,838(2)	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)	05/22/2026		M			312	(3)	02/22/2028(3)	Common Stock	312	$0	2,188	D

Explanation of Responses:

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

2. The total amount of securities beneficially owned by the reporting person has been adjusted to correct two (2) scrivener's errors. (1) On May 7, 2024, a Form 4 was filed reporting a direct purchase of 20,700 shares by the reporting person; however, such shares were in fact purchased by indirect beneficial owner Kuyashii Primary Equities LLC; and (2) Form 4s were filed on February 26, 2025 and on February 27, 2025 to report tax withholdings in the aggregate amount of 2,994 shares, however there was no tax withholdings at that time because the reporting person was no longer providing services as an employee. The total number of securities beneficially owned and as reported in Table I has been adjusted accordingly to reflect the reporting person's current beneficial ownership as of the transaction date.

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.

Remarks:

	/s/ Lauren Welsh as attorney-in-fact for Darryl Rawlings	05/27/2026
	** 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.
* Form 4: SEC 1474 (03-26)