STOCK TITAN

[Form 4] TRUPANION, INC. Insider Trading Activity

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

Rhea-AI Filing Summary

Trupanion, Inc. Chief Legal Officer Asher Bearman reported routine equity compensation activity involving restricted stock units (RSUs) and related tax withholding. On May 22, 2026 and May 25, 2026, RSUs converted into common stock and the company withheld shares to cover income tax obligations.

Across these transactions, Bearman acquired 2,609 shares of common stock through RSU vesting and 844 shares were withheld by the issuer to satisfy tax withholding and remittance obligations, which the filing notes does not represent a sale by the reporting person. Following the latest transaction, Bearman directly owns 72,244 shares of Trupanion common stock.

Positive

  • None.

Negative

  • None.
Insider BEARMAN ASHER
Role Chief Legal Officer
Type Security Shares Price Value
Exercise Restricted Stock Unit (RSU) 125 $0.00 --
Exercise Common Stock 125 $0.00 --
Tax Withholding Common Stock 40 $21.86 $874.40
Exercise Restricted Stock Unit (RSU) 265 $0.00 --
Exercise Restricted Stock Unit (RSU) 8 $0.00 --
Exercise Restricted Stock Unit (RSU) 379 $0.00 --
Exercise Restricted Stock Unit (RSU) 1,832 $0.00 --
Exercise Common Stock 265 $0.00 --
Tax Withholding Common Stock 85 $21.98 $2K
Exercise Common Stock 8 $0.00 --
Tax Withholding Common Stock 2 $21.98 $43.96
Exercise Common Stock 379 $0.00 --
Tax Withholding Common Stock 122 $21.98 $3K
Exercise Common Stock 1,832 $0.00 --
Tax Withholding Common Stock 595 $21.98 $13K
Holdings After Transaction: Restricted Stock Unit (RSU) — 625 shares (Direct, null); Common Stock — 72,284 shares (Direct, null)
Footnotes (1)
  1. Restricted stock units convert into common stock on a one-for-one basis. 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. On February 27, 2025, the reporting person was granted 2,122 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. On February 27, 2025, the reporting person was granted 70 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. On August 15, 2025, the reporting person was granted 3,032 restricted stock units (RSUs). The RSUs vest and convert into common stock of the Issuer as to 1/8th of the total shares on November 22, 2025, after which 1/8th of the total shares vest quarterly, subject to continued service through each vest date. On February 20, 2026, the reporting person was granted 14,656 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. On August 14, 2023, the Reporting Person was granted 1,999 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, 2024, after which 1/16th of the total shares vest quarterly, subject to continued service through each vest date.
RSUs converted to common stock 2,609 shares Total derivative exercises reported in this Form 4
Shares withheld for taxes 844 shares Used to satisfy income tax withholding obligations
Post-transaction holdings 72,244 shares Common stock directly owned after May 25, 2026
Tax withholding price May 22 $21.98 per share Price used for several F-code tax-withholding entries
Tax withholding price May 25 $21.86 per share Price for 40-share F-code tax-withholding entry
Exercise transactions 5 entries M-code derivative exercises converting RSUs into common stock
Tax-withholding transactions 5 entries F-code dispositions for tax withholding and remittance
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.
income tax withholding and remittance obligations financial
"Shares of common stock were withheld to satisfy income tax withholding and remittance obligations."
vest and convert into common stock financial
"The RSUs vest and convert into common stock of the Issuer as to 1/8th of the total shares."
derivative security financial
"Transaction code M reflects exercise or conversion of a 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.
Form 4 regulatory
"This Form 4 discloses the shares of common stock that have been withheld by the issuer."
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.
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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*
BEARMAN ASHER

(Last)(First)(Middle)
C/O TRUPANION, INC.
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 Legal 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 Stock05/22/2026M265A(1)70,744D
Common Stock05/22/2026F85(2)D$21.9870,659D
Common Stock05/22/2026M8A(1)70,667D
Common Stock05/22/2026F2(2)D$21.9870,665D
Common Stock05/22/2026M379A(1)71,044D
Common Stock05/22/2026F122(2)D$21.9870,922D
Common Stock05/22/2026M1,832A(1)72,754D
Common Stock05/22/2026F595(2)D$21.9872,159D
Common Stock05/25/2026M125A(1)72,284D
Common Stock05/25/2026F40(2)D$21.8672,244D
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)05/22/2026M265 (3)02/22/2027(3)Common Stock265$0796D
Restricted Stock Unit (RSU)(1)05/22/2026M8 (4)02/22/2027(4)Common Stock8$027D
Restricted Stock Unit (RSU)(1)05/22/2026M379 (5)08/22/2027(5)Common Stock379$01,895D
Restricted Stock Unit (RSU)(1)05/22/2026M1,832 (6)02/22/2028(6)Common Stock1,832$012,824D
Restricted Stock Unit (RSU)(1)05/25/2026M125 (7)08/25/2027(7)Common Stock125$0625D
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 2,122 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 27, 2025, the reporting person was granted 70 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 August 15, 2025, the reporting person was granted 3,032 restricted stock units (RSUs). The RSUs vest and convert into common stock of the Issuer as to 1/8th of the total shares on November 22, 2025, after which 1/8th of the total shares vest quarterly, subject to continued service through each vest date.
6. On February 20, 2026, the reporting person was granted 14,656 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.
7. On August 14, 2023, the Reporting Person was granted 1,999 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, 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 Asher Bearman05/27/2026
** 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)