TRUP · Trupanion, Inc.

The exercise and sale reported were effected pursuant to a Rule 10b5-1 (c) trading plan adopted by reporting person on May 11, 2026, in order to implement a plan of financial diversification. Accordingly, the reporting person had no discretion with regard to the timing of the transaction.

The exercise and sale reported were effected pursuant to a Rule 10b5-1 trading plan adopted by reporting person on August 20, 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.

The sale reported is effected pursuant to a Rule 10b5-1 trading plan adopted by reporting person on August 20, 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.

On July 22, 2016, the reporting person was granted 8,500 stock options. The stock options vested as to 25% of the total shares on July 22, 2017, and then 1/48th of the total stock options vested monthly thereafter, with 100% of the total shares vested and exercisable on July 22, 2020, subject to the reporting person's provision of service to the issuer on each vesting date.

The reported price in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $21.95 to $22.04 per share, inclusive. The reporting person undertakes to provide to the issuer, any security holder of the issuer, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the range set forth in this footnote (1).

The sale reported is effected pursuant to a Rule 10b5-1 trading plan adopted by reporting person on August 20, 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.

The reported price in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $21.220 to $22.085 per share, inclusive. The reporting person undertakes to provide to the issuer, any security holder of the issuer, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the range set forth in this footnote (2).

The sale reported is effected pursuant to a Rule 10b5-1 trading plan adopted by reporting person on May 19, 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.

The reported price in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $21.50 to $22.50 per share, inclusive. The reporting person undertakes to provide to the issuer, any security holder of the issuer, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the range set forth in this footnote (4).

The sale reported is effected pursuant to a Rule 10b5-1 trading plan adopted by reporting person on May 19, 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.

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

On February 27, 2023, the reporting person was granted 495 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, 2024, after which 1/16th of the total shares vest quarterly, subject to continued service through each vest date.

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

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

On August 14, 2023, the reporting person was granted 5,410 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.

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.

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.

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.

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.

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

On February 27, 2023, the reporting person was granted 649 restricted stock units (RSUs). The RSUs vested and converted into common stock of the Issuer as to 1/4th of the total shares on February 25, 2024, after which 1/16th of the total shares vest quarterly, subject to continued service through each vest date.

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.

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.

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

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.

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

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.

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.

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.

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.

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

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

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

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

On November 13, 2023, the reporting person was granted 60,000 restricted stock units (RSUs). The RSUs vest and convert into common stock of the Issuer as to 1/4th of the total shares on 11/25/24, after which 1/16th of the total shares vest quarterly, subject to continued service through each vest date.

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.

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.

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

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

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

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

On August 14, 2023, the reporting person was granted 434 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.

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

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

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.

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

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

On May 15, 2023, the reporting person was granted 277 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.

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

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.

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.

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

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.

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.

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

On August 12, 2022, the reporting person was granted 3,738 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, 2023, after which 1/16th of the total shares vest quarterly, subject to continued service through each vest date.

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

On August 14, 2023, the reporting person was granted 5,655 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.

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

On February 20, 2026, the reporting person was granted 12,260 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.