Simon Wheeler - 22 May 2026 Form 4 Insider Report for TRUPANION, INC. (TRUP)

Reporting relationship: EVP, Trupanion International
Issuer ticker: TRUP
Reported as of: 22 May 2026
Net transaction value: $0
SEC form: 4
Accepted by SEC: 27 May 2026, 21:57:06 UTC
Prior SEC filing: 27 Feb 2026
Source filing: View source filing
Reporting owner signature: /s/ Lauren Welsh as attorney-in-fact for Simon Wheeler

Key filing fact

Simon Wheeler filed Form 4 for TRUPANION, INC. (TRUP) on 27 May 2026.

Key facts

This page summarizes Simon Wheeler's Form 4 filing for TRUPANION, INC. (TRUP).
12 reported transactions and 4 derivative rows are listed below.
Accepted by SEC: 27 May 2026, 21:57.

Change

Previous filing in this sequence was filed on 27 Feb 2026.
Current net transaction value: $0.

Research use

This tells you what this filing adds before you inspect full transaction and derivative tables.
You can trace every row back to the original SEC filing document.

Evidence

Filed on Form 4

Ownership activity is grounded in SEC Form 4 disclosures.

View source filing

Reporting Owners (1)

CIK 0001966923 Primary reporting owner

WHEELER SIMON

Relationship: EVP, Trupanion International
Address: 4TH FLOOR CHARTER HOUSE, WOODLANDS ROAD, ALTRINCHAM, UNITED KINGDOM
Signature: /s/ Lauren Welsh as attorney-in-fact for Simon Wheeler
Signature date: 27 May 2026

This filing has been restated. Open the amended filing.

Reported non-derivative transactions

Shares, units, or other non-derivative securities reported in this filing.

TRUP transaction

Common Stock

Options Exercise

Transaction value
Shares: +937
Change %: +4.1%
Price
Shares after: 24,024
Date: 22 May 2026
Ownership: Direct
Footnotes: F1

TRUP transaction

Common Stock

Tax liability

Transaction value
Shares: -440
Change %: -1.8%
Price: $21.98^*
Shares after: 23,584
Date: 22 May 2026
Ownership: Direct
Footnotes: F2

TRUP transaction

Common Stock

Options Exercise

Transaction value
Shares: +527
Change %: +2.2%
Price
Shares after: 24,111
Date: 22 May 2026
Ownership: Direct
Footnotes: F1

TRUP transaction

Common Stock

Tax liability

Transaction value
Shares: -247
Change %: -1%
Price: $21.98^*
Shares after: 23,864
Date: 22 May 2026
Ownership: Direct
Footnotes: F2

TRUP transaction

Common Stock

Options Exercise

Transaction value
Shares: +384
Change %: +1.6%
Price
Shares after: 24,248
Date: 22 May 2026
Ownership: Direct
Footnotes: F1

TRUP transaction

Common Stock

Tax liability

Transaction value
Shares: -180
Change %: -0.74%
Price: $21.98^*
Shares after: 24,068
Date: 22 May 2026
Ownership: Direct
Footnotes: F2

TRUP transaction

Common Stock

Options Exercise

Transaction value
Shares: +321
Change %: +1.3%
Price
Shares after: 24,389
Date: 25 May 2026
Ownership: Direct
Footnotes: F1

TRUP transaction

Common Stock

Tax liability

Transaction value
Shares: -150
Change %: -0.62%
Price: $21.86^*
Shares after: 24,239
Date: 25 May 2026
Ownership: Direct
Footnotes: F2

Reported derivative securities

Options, warrants, convertible securities, or similar derivative positions disclosed in the filing.

TRUP transaction Derivative

Restricted Stock Unit (RSU)

Options Exercise

Transaction value
Shares: -527
Change %: -25%
Price: $0.000000^*
Shares after: 1,583
Date: 22 May 2026
Ownership: Direct
Underlying class: Common Stock
Underlying amount: 527
Exercise price
Footnotes: F1, F3

TRUP transaction Derivative

Restricted Stock Unit (RSU)

Options Exercise

Transaction value
Shares: -384
Change %: -12%
Price: $0.000000^*
Shares after: 2,695
Date: 22 May 2026
Ownership: Direct
Underlying class: Common Stock
Underlying amount: 384
Exercise price
Footnotes: F1, F4

TRUP transaction Derivative

Restricted Stock Unit (RSU)

Options Exercise

Transaction value
Shares: -937
Change %: -11%
Price: $0.000000^*
Shares after: 7,501
Date: 22 May 2026
Ownership: Direct
Underlying class: Common Stock
Underlying amount: 937
Exercise price
Footnotes: F1, F5

TRUP transaction Derivative

Restricted Stock Unit (RSU)

Options Exercise

Transaction value
Shares: -321
Change %: -17%
Price: $0.000000^*
Shares after: 1,608
Date: 25 May 2026
Ownership: Direct
Underlying class: Common Stock
Underlying amount: 321
Exercise price
Footnotes: F1, F6

^* marks a reported price that did not pass the local price check.

Additional SEC filing notes

Filing notes and footnotes

Explanation of responses 6 footnotes

Footnote F1

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

Footnote 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.

Footnote 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.

Footnote 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.

Footnote 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.

Footnote 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.