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

Reporting relationship: Director
Issuer ticker: TRUP
Reported as of: 22 May 2026
Net transaction value: $0
SEC form: 4
Accepted by SEC: 27 May 2026, 21:57:00 UTC
Prior SEC filing: 08 May 2026
Source filing: View source filing
Reporting owner signature: /s/ Lauren Welsh as attorney-in-fact for Darryl Rawlings

Key filing fact

Darryl Rawlings filed Form 4 for TRUPANION, INC. (TRUP) on 27 May 2026.

Key facts

This page summarizes Darryl Rawlings's Form 4 filing for TRUPANION, INC. (TRUP).
2 reported transactions and 1 derivative row are listed below.
Accepted by SEC: 27 May 2026, 21:57.

Change

Previous filing in this sequence was filed on 08 May 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 0001611679 Primary reporting owner

RAWLINGS DARRYL

Relationship: Director
Address: C/O TRUPANION, INC., 6100 4TH AVENUE SOUTH, SUITE 200, SEATTLE
Signature: /s/ Lauren Welsh as attorney-in-fact for Darryl Rawlings
Signature date: 27 May 2026

Reported non-derivative transactions

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

TRUP transaction

Common Stock

Options Exercise

Transaction value
Shares: +312
Change %: +1.3%
Price
Shares after: 24,838
Date: 22 May 2026
Ownership: Direct
Footnotes: F1, 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: -312
Change %: -12%
Price: $0.000000^*
Shares after: 2,188
Date: 22 May 2026
Ownership: Direct
Underlying class: Common Stock
Underlying amount: 312
Exercise price
Footnotes: F1, F3

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

Additional SEC filing notes

Filing notes and footnotes

Explanation of responses 3 footnotes

Footnote F1

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

Footnote F2

The total amount of securities beneficially owned by the reporting person has been adjusted to correct two (2) scrivener's errors. (1) On May 7, 2024, a Form 4 was filed reporting a direct purchase of 20,700 shares by the reporting person; however, such shares were in fact purchased by indirect beneficial owner Kuyashii Primary Equities LLC; and (2) Form 4s were filed on February 26, 2025 and on February 27, 2025 to report tax withholdings in the aggregate amount of 2,994 shares, however there was no tax withholdings at that time because the reporting person was no longer providing services as an employee. The total number of securities beneficially owned and as reported in Table I has been adjusted accordingly to reflect the reporting person's current beneficial ownership as of the transaction date.

Footnote F3

On February 27, 2024, the reporting person was granted 5,000 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 22, 2025, after which 1/16th of the total shares vest quarterly, subject to continued service through each vest date.