GALLAGHER JOHN R 4
4 · TRUPANION, INC. · Filed May 27, 2026
Research Summary
AI-generated summary of this filing
TRUPANION COO John R Gallagher Exercises RSUs; Shares Withheld
What Happened
John R. Gallagher, COO of Trupanion, reported the conversion/exercise of restricted stock units (RSUs) into common stock on May 22 and May 25, 2026. In total 6,793 RSUs converted into common shares. To satisfy income tax withholding, the issuer withheld 1,651 of those shares (reported as dispositions for tax withholding) for total withholding proceeds of $36,275 (≈ $21.98/share on 5/22 and $21.86/share on 5/25). The conversion lines show $0 proceeds for the derivative conversion itself (i.e., the RSUs converted into shares rather than producing cash).
Key Details
- Transaction dates: May 22, 2026 and May 25, 2026.
- Converted/acquired shares: 6,793 total (865 + 3,327 + 2,076 on 5/22; 29 + 451 + 45 on 5/25).
- Shares withheld for taxes (disposed): 1,651 total (1,525 on 5/22; 126 on 5/25) for $36,275 total (breakdown: $33,520 on 5/22 and $2,755 on 5/25).
- Reported price used for withholding: $21.98 (May 22) and $21.86 (May 25).
- Footnotes: F1/F2 indicate RSUs convert 1-for-1 and that withheld shares are to satisfy tax obligations (not an open-market sale). Relevant grants/vesting schedules noted in F3–F8 (grants from 2023–2026; F5 shows a Feb 20, 2026 grant with partial vesting on May 22, 2026).
- Shares owned after the transaction: not provided in the excerpt of the filing.
- Filing date: Form 4 filed May 27, 2026 for transactions on May 22 & 25 — check filing timeliness against SEC rules if timing is a concern.
Context
- These transactions are RSU conversions (derivative code M) with shares withheld to meet tax withholding obligations (code F). The withheld shares are issuer remittances to cover taxes and do not represent an active sale by Gallagher.
- For retail investors: this is routine compensation vesting and tax withholding rather than a market sale or a buy that signals insider conviction.
Insider Transaction Report
Form 4
TRUPANION, INC.TRUP
GALLAGHER JOHN R
Chief Operating Officer
Transactions
- Exercise/Conversion
Common Stock
[F1]2026-05-22+865→ 32,391 total - Tax Payment
Common Stock
[F2]2026-05-22$21.98/sh−210$4,616→ 32,181 total - Exercise/Conversion
Common Stock
[F1]2026-05-22+3,327→ 35,508 total - Tax Payment
Common Stock
[F2]2026-05-22$21.98/sh−810$17,804→ 34,698 total - Exercise/Conversion
Common Stock
[F1]2026-05-22+2,076→ 36,774 total - Tax Payment
Common Stock
[F2]2026-05-22$21.98/sh−505$11,100→ 36,269 total - Exercise/Conversion
Common Stock
[F1]2026-05-25+29→ 36,298 total - Tax Payment
Common Stock
[F2]2026-05-25$21.86/sh−7$153→ 36,291 total - Exercise/Conversion
Common Stock
[F1]2026-05-25+451→ 36,742 total - Tax Payment
Common Stock
[F2]2026-05-25$21.86/sh−109$2,383→ 36,633 total - Exercise/Conversion
Common Stock
[F1]2026-05-25+45→ 36,678 total - Tax Payment
Common Stock
[F2]2026-05-25$21.86/sh−10$219→ 36,668 total - Exercise/Conversion
Restricted Stock Unit (RSU)
[F1][F3]2026-05-22−865→ 8,649 totalExp: 2028-11-22→ Common Stock (865 underlying) - Exercise/Conversion
Restricted Stock Unit (RSU)
[F1][F4]2026-05-22−3,327→ 9,983 totalExp: 2027-02-22→ Common Stock (3,327 underlying) - Exercise/Conversion
Restricted Stock Unit (RSU)
[F1][F5]2026-05-22−2,076→ 14,533 totalExp: 2028-02-22→ Common Stock (2,076 underlying) - Exercise/Conversion
Restricted Stock Unit (RSU)
[F1][F6]2026-05-25−29→ 115 totalExp: 2027-05-25→ Common Stock (29 underlying) - Exercise/Conversion
Restricted Stock Unit (RSU)
[F1][F7]2026-05-25−451→ 2,258 totalExp: 2027-08-25→ Common Stock (451 underlying) - Exercise/Conversion
Restricted Stock Unit (RSU)
[F1][F8]2026-05-25−45→ 225 totalExp: 2027-08-25→ Common Stock (45 underlying)
Footnotes (8)
- [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]On November 12, 2024, the reporting person was granted 13,838 restricted stock units (RSUs). The RSUs vest and convert into common stock of the Issuer as to 1/4th of the total shares on November 22, 2025, after which 1/16th of the total shares vest quarterly, subject to continued service through each vest date.
- [F4]On February 27, 2025, the reporting person was granted 26,619 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.
- [F5]On February 20, 2026, the reporting person was granted 16,609 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.
- [F6]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.
- [F7]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.
- [F8]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.
Signature
/s/ Lauren Welsh as attorney-in-fact for John R. Gallagher|2026-05-27