Tooth Margaret 4

What Happened

• Margaret Tooth, CEO and director of Trupanion, converted (exercised/converted) a total of 19,042 shares on May 22 and May 25, 2026 through the vesting/conversion of restricted stock units (RSUs). The issuer withheld 6,999 of those shares to cover tax withholding obligations (reported as dispositions with a withholding price of $21.98 per share, aggregate $153,839). Separately, Tooth executed an open-market sale of 491 shares on May 25, 2026 at $21.86, netting $10,733. The conversion/vesting activity is generally neutral (vesting/award), while the small open-market sale is an actual disposition by the insider.

Key Details

• Transaction dates: primary conversions on 2026-05-22 and 2026-05-25; open-market sale on 2026-05-25.
• Conversion (derivative code M): 19,042 shares acquired via RSU conversion (multiple grants/vesting events).
• Tax withholding (code F): 6,999 shares withheld at $21.98 (listed totals $153,839); these withholdings satisfy issuer tax remittance and “do not represent a sale by the reporting person” per footnote F3.
• Open-market sale (code S): 491 shares sold at $21.86 for $10,733.
• Footnotes: RSUs convert 1:1 to common stock (F1); multiple RSU grant schedules noted (F4–F8) including grants on Feb 20, 2026 (F7), Feb 27, 2025 (F6), Aug 19, 2024 (F5), Feb 27, 2024 (F4), and Aug 14, 2023 (F8). F2 notes a correction to previously reported beneficial ownership.
• Filing: Form 4 filed 2026-05-27 reporting transactions with dates 2026-05-22 and 2026-05-25. The May 22 transactions were reported five days later than the transaction date (outside the typical two-business-day Form 4 deadline), while the May 25 trade was filed within two business days.

Context

• These were primarily RSU vesting/conversion events (derivative conversions), not stock purchases — the company withheld shares to cover tax obligations (a common cashless-withholding procedure). The small open-market sale (491 shares) is the only transaction that represents an actual sale by the CEO in this filing.
• No explicit post-transaction beneficial ownership total was provided in the data supplied here (Footnote F2 indicates prior holdings were corrected on the filing).