RAWLINGS DARRYL 4
4 · TRUPANION, INC. · Filed May 27, 2026
Research Summary
AI-generated summary of this filing
Trupanion (TRUP) Director Darryl Rawlings Exercises RSUs (312 shares)
What Happened
- Darryl Rawlings, a director of Trupanion, reported the conversion/exercise of 312 derivative units on May 22, 2026. The Form 4 shows 312 shares acquired via conversion/exercise and an equal 312-share disposition at $0.00, resulting in no reported cash proceeds and a net zero change in held shares on that transaction date.
- The filing treats the items as derivative conversions (transaction code M). No dollar value for the acquisition was reported (Acquired: N/A; Disposed: $0.00).
Key Details
- Transaction date: 2026-05-22; Form 4 filed: 2026-05-27 (filed 5 days after the transaction — later than the typical 2-business-day Form 4 deadline).
- Shares involved: 312 acquired via conversion; 312 disposed at $0.00 (net zero change).
- Shares owned after transaction: not specified in the excerpt; the filing states that beneficial ownership figures were adjusted to correct prior scrivener’s errors (see footnote summary).
- Relevant footnotes:
- F1: Restricted stock units (RSUs) convert one-for-one into common stock.
- F2: Reporting person’s beneficial ownership totals were corrected for prior scrivener’s errors.
- F3: The reporting person was granted 5,000 RSUs on Feb 27, 2024, with an initial 1/4 vesting on Feb 22, 2025 and subsequent 1/16th quarterly vesting (312.5 shares ≈ 312).
- Filing timeliness: marked late relative to the usual 2-business-day Form 4 requirement (filed 5 days after the reported transaction).
Context
- The filings are consistent with routine RSU vesting: vested RSUs convert into shares (derivative conversion). The simultaneous disposition at $0.00 typically indicates shares were surrendered/withheld rather than sold for cash (commonly done to satisfy tax withholding), which explains the net-zero change. This type of entry is generally administrative and does not necessarily indicate a buy or sell signal about the insider’s market view.
Insider Transaction Report
Form 4
TRUPANION, INC.TRUP
RAWLINGS DARRYL
Director
Transactions
- Exercise/Conversion
Common Stock
[F1][F2]2026-05-22+312→ 24,838 total - Exercise/Conversion
Restricted Stock Unit (RSU)
[F1][F3]2026-05-22−312→ 2,188 totalExp: 2028-02-22→ Common Stock (312 underlying)
Footnotes (3)
- [F1]Restricted stock units convert into common stock on a one-for-one basis.
- [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.
- [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.
Signature
/s/ Lauren Welsh as attorney-in-fact for Darryl Rawlings|2026-05-27