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Trupanion (NASDAQ: TRUP) 10% owner’s RSUs vest as shares withheld for taxes

Filing Impact
(Neutral)
Filing Sentiment
(Neutral)
Form Type
4

Rhea-AI Filing Summary

TRUPANION, INC. executive Simon Wheeler, EVP Trupanion International, reported routine equity compensation activity involving restricted stock units (RSUs) that convert into common stock on a one-for-one basis. On May 22 and May 25, 2026, RSUs vested and were exercised into a total of 2,169 shares of common stock through multiple transactions coded "M" for derivative exercises.

In connection with these vestings, 1,017 common shares coded "F" were withheld by the issuer at prices of $21.98 and $21.86 per share to satisfy income tax withholding and remittance obligations, which the filing explicitly states do not represent sales by Wheeler. After these transactions, Wheeler directly owned 24,239 shares of common stock, and still held RSU awards originally granted on August 14, 2023, February 27, 2024, February 27, 2025, and February 20, 2026 that continue to vest over time, subject to continued service.

Positive

  • None.

Negative

  • None.
Insider WHEELER SIMON
Role EVP, Trupanion International
Type Security Shares Price Value
Exercise Restricted Stock Unit (RSU) 321 $0.00 $0.00
Exercise Common Stock 321 $0.00 $0.00
Exercise Price or Tax Liability Common Stock 150 $21.86 $3K
Exercise Restricted Stock Unit (RSU) 527 $0.00 $0.00
Exercise Restricted Stock Unit (RSU) 384 $0.00 $0.00
Exercise Restricted Stock Unit (RSU) 937 $0.00 $0.00
Exercise Common Stock 937 $0.00 $0.00
Exercise Price or Tax Liability Common Stock 440 $21.98 $10K
Exercise Common Stock 527 $0.00 $0.00
Exercise Price or Tax Liability Common Stock 247 $21.98 $5K
Exercise Common Stock 384 $0.00 $0.00
Exercise Price or Tax Liability Common Stock 180 $21.98 $4K
Holdings After Transaction: Restricted Stock Unit (RSU) — 13,387 shares (Direct); Common Stock — 24,239 shares (Direct)
Footnotes (6)
  1. F1. Restricted stock units convert into common stock on a one-for-one basis.
  2. F2. 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. F3. On February 27, 2025, the reporting person was granted 4,219 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, 2025, after which 1/8th of the total shares vest quarterly, subject to continued service through each vest date.
  4. F4. On February 20, 2026, the reporting person was granted 3,079 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, 2026, after which 1/8th of the total shares vest quarterly, subject to continued service through each vest date.
  5. F5. On February 27, 2024, the reporting person was granted 15,000 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 25, 2025, after which 1/16th of the total shares vest quarterly, subject to continued service through each vest date.
  6. F6. On August 14, 2023, the reporting person was granted 5,144 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.

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Form 4 Insider Transactions: What Each Field Means →
SEC Form 4
FORM 4UNITED 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*
WHEELER SIMON
(Last)(First)(Middle)
4TH FLOOR CHARTER HOUSE
WOODLANDS ROAD
(Street)
ALTRINCHAMWA14 1HF
(City)(State)(Zip)
UNITED KINGDOM
(Country)		2. Issuer Name and Ticker or Trading Symbol
TRUPANION, INC. [ TRUP ] 		5. Relationship of Reporting Person(s) to Issuer
(Check all applicable)
Director10% Owner
XOfficer (give title below)Other (specify below)
EVP, Trupanion International
2a. Foreign Trading Symbol
3. Date of Earliest Transaction (Month/Day/Year)
05/22/2026		6. Individual or Joint/Group Filing (Check Applicable Line)
XForm 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)
CodeVAmount(A) or (D)Price
Common Stock05/22/2026M937A(1)24,024D
Common Stock05/22/2026F440(2)D$21.9823,584D
Common Stock05/22/2026M527A(1)24,111D
Common Stock05/22/2026F247(2)D$21.9823,864D
Common Stock05/22/2026M384A(1)24,248D
Common Stock05/22/2026F180(2)D$21.9824,068D
Common Stock05/25/2026M321A(1)24,389D
Common Stock05/25/2026F150(2)D$21.8624,239D
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)
CodeV(A)(D)Date ExercisableExpiration DateTitleAmount or Number of Shares
Restricted Stock Unit (RSU)(1)05/22/2026M527 (3)02/22/2027(3)Common Stock527$01,583D
Restricted Stock Unit (RSU)(1)05/22/2026M384 (4)02/22/2028(4)Common Stock384$02,695D
Restricted Stock Unit (RSU)(1)05/22/2026M937 (5)02/25/2028(5)Common Stock937$07,501D
Restricted Stock Unit (RSU)(1)05/25/2026M321 (6)08/25/2027(6)Common Stock321$01,608D
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, 2025, the reporting person was granted 4,219 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, 2025, after which 1/8th of the total shares vest quarterly, subject to continued service through each vest date.
4. On February 20, 2026, the reporting person was granted 3,079 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, 2026, 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 15,000 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 25, 2025, 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 5,144 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/ Lauren Welsh as attorney-in-fact for Simon Wheeler05/27/2026
** Signature of Reporting PersonDate
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)

Source: View Original Filing on SEC EDGAR