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TRUPANION, INC.·4

May 27, 9:41 PM ET

Tooth Margaret 4

4 · TRUPANION, INC. · Filed May 27, 2026

Research Summary

AI-generated summary of this filing

Updated

Trupanion (TRUP) CEO Margaret Tooth Converts RSUs, Sells 491 Shares

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).

Insider Transaction Report

Form 4
Period: 2026-05-22
TRUPANION, INC.TRUP
Tooth Margaret
DirectorCEO
Transactions
  • Exercise/Conversion

    Common Stock

    [F1][F2]
    2026-05-22+312→ 165,139 total
  • Tax Payment

    Common Stock

    [F3]
    2026-05-22$21.98/sh−122$2,682→ 165,017 total
  • Exercise/Conversion

    Common Stock

    [F1]
    2026-05-22+3,043→ 168,060 total
  • Tax Payment

    Common Stock

    [F3]
    2026-05-22$21.98/sh−1,197$26,310→ 166,863 total
  • Exercise/Conversion

    Common Stock

    [F1]
    2026-05-22+6,250→ 173,113 total
  • Tax Payment

    Common Stock

    [F3]
    2026-05-22$21.98/sh−2,459$54,049→ 170,654 total
  • Exercise/Conversion

    Common Stock

    [F1]
    2026-05-22+8,187→ 178,841 total
  • Tax Payment

    Common Stock

    [F3]
    2026-05-22$21.98/sh−3,221$70,798→ 175,620 total
  • Exercise/Conversion

    Common Stock

    [F1]
    2026-05-25+1,250→ 176,870 total
  • Sale

    Common Stock

    [F3]
    2026-05-25$21.86/sh−491$10,733→ 176,379 total
  • Exercise/Conversion

    Restricted Stock Unit (RSU)

    [F1][F4]
    2026-05-22−312→ 2,188 total
    Exp: 2028-02-22→ Common Stock (312 underlying)
  • Exercise/Conversion

    Restricted Stock Unit (RSU)

    [F1][F5]
    2026-05-22−3,043→ 27,382 total
    Exp: 2028-08-22→ Common Stock (3,043 underlying)
  • Exercise/Conversion

    Restricted Stock Unit (RSU)

    [F1][F6]
    2026-05-22−6,250→ 18,750 total
    Exp: 2027-02-22→ Common Stock (6,250 underlying)
  • Exercise/Conversion

    Restricted Stock Unit (RSU)

    [F1][F7]
    2026-05-22−8,187→ 57,310 total
    Exp: 2028-02-22→ Common Stock (8,187 underlying)
  • Exercise/Conversion

    Restricted Stock Unit (RSU)

    [F1][F8]
    2026-05-25−1,250→ 6,250 total
    Exp: 2027-08-25→ Common Stock (1,250 underlying)
Footnotes (8)
  • [F1]Restricted stock units convert into common stock on a one-for-one basis.
  • [F2]This footnote corrects an administrative error in the reporting of previously disclosed holdings. 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]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.
  • [F4]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.
  • [F5]On August 19, 2024, the reporting person was granted 48,679 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 22, 2025, after which 1/16th of the total shares vest quarterly, subject to continued service through each vest date.
  • [F6]On February 27, 2025, the reporting person was granted 50,000 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.
  • [F7]On February 20, 2026, the reporting person was granted 65,497 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.
  • [F8]On August 14, 2023, the reporting person was granted 20,000 restricted stock units (RSUs). The RSUs vest and convert into common stock of the Issuer as to 1/4th of the total shares on 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 Margaret Tooth|2026-05-27

Documents

1 file
  • 4
    wk-form4_1779932493.xmlPrimary

    FORM 4