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Trupanion (NASDAQ: TRUP) COO reports RSU vesting and tax withholding

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(Neutral)
Form Type
4

Rhea-AI Filing Summary

TRUPANION, INC. Chief Operating Officer John R. Gallagher reported a series of equity compensation transactions involving restricted stock units and common stock on May 22 and 25, 2026.

Gallagher exercised derivative awards to acquire a total of 6,793 shares of common stock, according to the transaction summary. In connection with these vestings, 1,651 shares of common stock were withheld by the company to satisfy income tax withholding and remittance obligations at prices of about $21.98 and $21.86 per share. A footnote clarifies that these tax-withholding entries do not represent open-market sales by Gallagher.

After these transactions, Gallagher directly holds 36,291 shares of Trupanion common stock, reflecting routine equity compensation vesting and associated tax settlements rather than discretionary market buying or selling.

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Insider GALLAGHER JOHN R
Role Chief Operating Officer
Type Security Shares Price Value
Exercise Restricted Stock Unit (RSU) 29 $0.00 $0.00
Exercise Restricted Stock Unit (RSU) 451 $0.00 $0.00
Exercise Restricted Stock Unit (RSU) 45 $0.00 $0.00
Exercise Common Stock 29 $0.00 $0.00
Exercise Price or Tax Liability Common Stock 7 $21.86 $153.02
Exercise Common Stock 451 $0.00 $0.00
Exercise Price or Tax Liability Common Stock 109 $21.86 $2K
Exercise Common Stock 45 $0.00 $0.00
Exercise Price or Tax Liability Common Stock 10 $21.86 $218.60
Exercise Restricted Stock Unit (RSU) 865 $0.00 $0.00
Exercise Restricted Stock Unit (RSU) 3,327 $0.00 $0.00
Exercise Restricted Stock Unit (RSU) 2,076 $0.00 $0.00
Exercise Common Stock 865 $0.00 $0.00
Exercise Price or Tax Liability Common Stock 210 $21.98 $5K
Exercise Common Stock 3,327 $0.00 $0.00
Exercise Price or Tax Liability Common Stock 810 $21.98 $18K
Exercise Common Stock 2,076 $0.00 $0.00
Exercise Price or Tax Liability Common Stock 505 $21.98 $11K
Holdings After Transaction: Restricted Stock Unit (RSU) — 35,763 shares (Direct); Common Stock — 36,668 shares (Direct)
Footnotes (8)
  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 November 12, 2024, the reporting person was granted 13,838 restricted stock units (RSUs). The RSUs vest and convert into common stock of the Issuer as to 1/4th of the total shares on November 22, 2025, after which 1/16th of the total shares vest quarterly, subject to continued service through each vest date.
  4. F4. On February 27, 2025, the reporting person was granted 26,619 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.
  5. F5. On February 20, 2026, the reporting person was granted 16,609 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.
  6. F6. On May 15, 2023, the reporting person was granted 460 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.
  7. F7. On August 14, 2023, the reporting person was granted 7,223 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.
  8. F8. On August 14, 2023, the reporting person was granted 721 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.
RSU exercises 6,793 shares Derivative exercises and conversions reported for May 22–25, 2026
Tax withholding shares 1,651 shares Shares withheld to satisfy income tax obligations on RSU vesting
Tax withholding price $21.98 per share F-code dispositions on May 22, 2026
Tax withholding price $21.86 per share F-code dispositions on May 25, 2026
Post-transaction holdings 36,291 shares Common stock directly owned after reported transactions
RSU conversion ratio 1:1 Restricted stock units convert into common stock one-for-one
Restricted stock units (RSUs) financial
"On November 12, 2024, the reporting person was granted 13,838 restricted stock units (RSUs)."
Restricted stock units (RSUs) are a type of company promise to give employees shares of stock in the future, usually after certain conditions like working for a set time. They are like a gift promised today that you receive later, which can become valuable if the company's stock price goes up. RSUs matter because they are a way companies reward employees and can be a significant part of compensation.
tax withholding financial
"shares of common stock that have been withheld by the issuer to satisfy its income tax withholding and remittance obligations"
Tax withholding is the practice of taking a portion of a payment—such as wages, dividends, or sale proceeds—before it reaches the recipient and sending that portion to the tax authority as an advance on the recipient’s eventual tax bill. For investors it matters because withholding reduces immediate cash received and affects after‑tax returns, estimated tax payments, and whether you may owe more or receive a refund when taxes are finally calculated, like having a small automatic savings set aside for your tax bill.
derivative security financial
"transaction_code_description": "Exercise or conversion of derivative security""
A derivative security is a financial contract whose value comes from the price or performance of something else, such as a stock, bond, commodity, or market index. For investors it acts like an insurance policy or a wager: it can be used to protect against losses, lock in prices, or amplify gains and losses, so it can change a portfolio’s risk and potential return without owning the underlying asset directly.
vesting financial
"The RSUs vest and convert into common stock of the Issuer as to 1/4th of the total shares"
Vesting is the process by which you earn full ownership of something, like company stock or a retirement benefit, over time. It’s like earning the right to keep a gift piece by piece the longer you stay with a company, making sure employees stay committed before they receive all the benefits.
Form 4 regulatory
"This Form 4 discloses the shares of common stock that have been withheld"
Form 4 is a official document that company insiders, such as executives or major shareholders, file with regulators whenever they buy or sell company shares. It provides transparency about how those with inside knowledge are trading, helping investors see if insiders are confident in the company's prospects or may be selling for personal reasons. This information can influence investor decisions by revealing insiders' perspectives on the company's value.

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

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FAQ

What did TRUP COO John R. Gallagher report in this Form 4?

John R. Gallagher reported routine equity compensation activity. He exercised restricted stock unit awards into Trupanion common stock, and shares were withheld by the company to cover tax obligations associated with those vestings, rather than representing open-market stock sales.

How many TRUP shares did the COO acquire through RSU exercises?

Gallagher exercised derivative awards covering 6,793 shares of Trupanion common stock. These exercises reflect restricted stock units converting into common shares as they vested, consistent with previously granted equity compensation awards described in the footnotes to the filing.

Were any of the TRUP COO’s reported transactions open-market stock sales?

The filing indicates no open-market sales. Footnotes state that 1,651 shares were withheld by Trupanion to satisfy income tax withholding and remittance obligations on RSU vesting, and that these tax-withholding entries do not represent sales by the reporting person.

At what prices were TRUP shares withheld for tax obligations?

Shares were withheld at prices of about $21.98 and $21.86 per share. These prices apply to the tax-withholding dispositions related to vested restricted stock units, as reflected in multiple F-code entries within the Form 4 transaction table.

How many TRUP shares does the COO own after these transactions?

Following the reported vesting and tax-withholding activity, Gallagher directly owns 36,291 shares of Trupanion common stock. This post-transaction holding reflects his remaining equity stake after the company withheld shares to meet income tax obligations on the RSU vestings.

What do the RSU footnotes in the TRUP Form 4 explain?

The footnotes explain grant dates and vesting schedules for several RSU awards. They note that restricted stock units convert into common stock on a one-for-one basis and vest in tranches over time, subject to Gallagher’s continued service with Trupanion through each vesting date.
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*
GALLAGHER JOHN R

(Last)(First)(Middle)
6100 4TH AVENUE S
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)
Director10% Owner
XOfficer (give title below)Other (specify below)
Chief Operating Officer
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 Stock05/22/2026M865A(1)32,391D
Common Stock05/22/2026F210(2)D$21.9832,181D
Common Stock05/22/2026M3,327A(1)35,508D
Common Stock05/22/2026F810(2)D$21.9834,698D
Common Stock05/22/2026M2,076A(1)36,774D
Common Stock05/22/2026F505(2)D$21.9836,269D
Common Stock05/25/2026M29A(1)36,298D
Common Stock05/25/2026F7(2)D$21.8636,291D
Common Stock05/25/2026M451A(1)36,742D
Common Stock05/25/2026F109(2)D$21.8636,633D
Common Stock05/25/2026M45A(1)36,678D
Common Stock05/25/2026F10(2)D$21.8636,668D
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)05/22/2026M865 (3)11/22/2028(3)Common Stock865$08,649D
Restricted Stock Unit (RSU)(1)05/22/2026M3,327 (4)02/22/2027(4)Common Stock3,327$09,983D
Restricted Stock Unit (RSU)(1)05/22/2026M2,076 (5)02/22/2028(5)Common Stock2,076$014,533D
Restricted Stock Unit (RSU)(1)05/25/2026M29 (6)05/25/2027(6)Common Stock29$0115D
Restricted Stock Unit (RSU)(1)05/25/2026M451 (7)08/25/2027(7)Common Stock451$02,258D
Restricted Stock Unit (RSU)(1)05/25/2026M45 (8)08/25/2027(8)Common Stock45$0225D
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 November 12, 2024, the reporting person was granted 13,838 restricted stock units (RSUs). The RSUs vest and convert into common stock of the Issuer as to 1/4th of the total shares on November 22, 2025, after which 1/16th of the total shares vest quarterly, subject to continued service through each vest date.
4. On February 27, 2025, the reporting person was granted 26,619 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.
5. On February 20, 2026, the reporting person was granted 16,609 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.
6. On May 15, 2023, the reporting person was granted 460 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.
7. On August 14, 2023, the reporting person was granted 7,223 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.
8. On August 14, 2023, the reporting person was granted 721 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 John R. Gallagher05/27/2026
** 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)