Margaret Tooth - 25 Nov 2025 Form 4 Insider Report for TRUPANION, INC. (TRUP)

Role
CEO, Director
Signature
/s/ Christina Poler as attorney-in-fact for Margaret Tooth
Issuer symbol
TRUP
Transactions as of
25 Nov 2025
Net transactions value
-$337,503
Form type
4
Filing time
26 Nov 2025, 18:27:25 UTC
Previous filing
25 Nov 2025
Next filing
22 Dec 2025
SEC
View on sec.gov

Reporting Owners (1)

Name Relationship Address Signature Signature date CIK
Tooth Margaret CEO, Director C/O TRUPANION, INC., 6100 4TH AVENUE SOUTH, SUITE 200, SEATTLE /s/ Christina Poler as attorney-in-fact for Margaret Tooth 26 Nov 2025 0001657025

Transactions Table

Type Sym Class Transaction Value $ Shares Change % * Price $ Shares After Date Ownership Footnotes
transaction TRUP Common Stock Options Exercise +1,250 +0.83% 152,212 25 Nov 2025 Direct F1
transaction TRUP Common Stock Tax liability $17,362 -491 -0.32% $35.36 151,721 25 Nov 2025 Direct F2
transaction TRUP Common Stock Options Exercise +3,266 +2.2% 154,987 25 Nov 2025 Direct F1
transaction TRUP Common Stock Tax liability $45,438 -1,285 -0.83% $35.36 153,702 25 Nov 2025 Direct F2
transaction TRUP Common Stock Options Exercise $71,440 +8,000 +5.2% $8.93 161,702 25 Nov 2025 Direct F3
transaction TRUP Common Stock Sale $282,480 -8,000 -4.9% $35.31 153,702 25 Nov 2025 Direct F3
transaction TRUP Common Stock Sale $63,664 -1,803 -1.2% $35.31 151,899 25 Nov 2025 Direct F3

Derivative Securities (e.g., puts, calls, warrants, options, convertible securities)

Type Sym Class Transaction Value $ Shares Change % * Price $ Shares After Date Underlying Class Amount Exercise Price Ownership Footnotes
transaction TRUP Restricted Stock Unit (RSU) Options Exercise $0 -1,250 -12% $0.000000 8,750 25 Nov 2025 Common Stock 1,250 Direct F1, F4
transaction TRUP Restricted Stock Unit (RSU) Options Exercise $0 -3,266 -50% $0.000000 3,266 25 Nov 2025 Common Stock 3,266 Direct F1, F5
transaction TRUP Stock Option (right to buy) Options Exercise $0 -8,000 -50% $0.000000 8,000 25 Nov 2025 Common Stock 8,000 $8.93 Direct F3, F6
* An asterisk sign (*) next to the price indicates that the price is likely invalid.

Buy Plan / Sale Plan: These are also open market purchases/sales of shares, but in this case the transaction is part of a trading plan. Rule 10b5-1 allows insiders to setup a trading plan to buy/sell stocks over a certain period of time. Since the purchases/sales are predetermined, this protects the insiders from violating insider trading law.

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).

Explanation of Responses:

Id Content
F1 Restricted stock units convert into common stock on a one-for-one basis.
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.
F3 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.
F4 On August 14, 2023, the reporting person was granted 20,000 restricted stock units (RSUs). The RSUs vest and convert into common stock of the Issuer as to 1/4th of the total shares on August 25, 2024, after which 1/16th of the total shares vest quarterly, subject to continued service through each vest date.
F5 On February 28, 2022, the Reporting Person was granted 52,250 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 February 25, 2023, after which 1/16th of the total shares vest quarterly, subject to continued service through each vest date.
F6 This stock option grant is fully vested.