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Trupanion director Darryl Rawlings exercised restricted stock units into common shares. On May 22, 2026, 312 RSUs converted into 312 shares of common stock, reflecting a one-for-one conversion ratio. Following this exercise, Rawlings directly held 24,838 common shares and 2,188 RSUs.
A footnote explains that his reported beneficial ownership has been adjusted to correct two scrivener's errors in prior Form 4 filings, reattributing a previously reported 20,700-share purchase to indirect beneficial owner Kuyashii Primary Equities LLC and removing 2,994 shares that had been reported as tax withholdings.
Trupanion, Inc. CEO Margaret Tooth reported a mix of stock transactions including a small open‑market sale and multiple RSU conversions. On May 25, 2026 she sold 491 shares of common stock in an open‑market transaction at $21.86 per share and held 176,379 shares afterward. On May 22–25, 2026 she exercised and converted a total of 19,042 restricted stock units into common stock at a $0.00 exercise price, while 6,999 shares were withheld by the company to cover tax obligations, which the filing states do not represent sales by her. The report also notes an administrative correction adjusting previously disclosed beneficial ownership to reflect her current holdings as of the transaction dates.
TRUPANION, INC. Chief Administration Officer Brenna McGibney reported compensation-related stock activity, with restricted stock units vesting into 6,431 shares of common stock on May 22 and May 25, 2026. The company withheld 3,439 shares at prices around $21.98 and $21.86 solely to cover tax obligations, not as open-market sales. Following these transactions, McGibney holds 11,265 common shares directly.
TRUPANION, INC. Chief Operating Officer John R. Gallagher reported a series of equity compensation transactions involving restricted stock units and common stock on May 22 and 25, 2026.
Gallagher exercised derivative awards to acquire a total of 6,793 shares of common stock, according to the transaction summary. In connection with these vestings, 1,651 shares of common stock were withheld by the company to satisfy income tax withholding and remittance obligations at prices of about $21.98 and $21.86 per share. A footnote clarifies that these tax-withholding entries do not represent open-market sales by Gallagher.
After these transactions, Gallagher directly holds 36,291 shares of Trupanion common stock, reflecting routine equity compensation vesting and associated tax settlements rather than discretionary market buying or selling.
TRUPANION, INC. director Bradley S. Powell reported an automatic equity compensation event. On May 22, 2026, 639 restricted stock units vested and converted into 639 shares of common stock at $0.00 per share under a previously granted RSU award.
The filing shows this as an exercise or conversion of a derivative security, not an open-market purchase or sale. Following the conversion, Powell directly holds 1,906 shares of Trupanion common stock. The RSUs convert into common stock on a one-for-one basis and were part of a 1,906-unit grant from November 14, 2025 that vested in three equal installments.
TRUPANION, INC. director Howard E. Rubin exercised previously granted restricted stock units that converted into a total of 318 shares of common stock on May 22, 2026. These RSUs convert into common stock on a one-for-one basis and were granted in connection with his service on boards of wholly-owned subsidiaries.
After these routine equity compensation-related conversions, Rubin directly holds 232,868 shares of Trupanion common stock. The filing shows only derivative exercises and no open‑market purchases or sales.
Trupanion EVP Steve Weinrauch reported routine equity compensation activity involving restricted stock units (RSUs) and related tax withholding. On May 22 and May 25, 2026, RSUs vested and converted into common stock, and the company withheld a total of 1,180 common shares at prices around $21.86–$21.98 per share to cover income tax obligations. The filing notes these tax-withholding dispositions do not represent open-market sales by Weinrauch. Across these vesting events, 4,857 RSUs converted into common stock. Following the transactions, Weinrauch holds 76,236 shares of Trupanion common stock directly.
TRUPANION, INC. Chief Financial Officer Fawwad Qureshi reported a mix of equity compensation vesting, tax withholding, and stock sales. On May 22 and May 25, 2026, he exercised restricted stock units to acquire a total of 13,744 shares of common stock at a conversion price of $0.00 per share. To cover income tax obligations tied to these vestings, the issuer withheld a total of 5,486 shares, which the filing clarifies do not represent sales by Qureshi.
On May 27, 2026, Qureshi sold an aggregate of 6,177 shares of common stock in open-market transactions at weighted average prices of about $22.63 and $22.17 per share, executed under a pre-arranged Rule 10b5-1 trading plan adopted on May 19, 2025. Following these transactions, he directly holds 2,081 shares of common stock. The filing also shows continuing holdings of restricted stock units that convert into common stock on a one-for-one basis, including 31,047 RSUs from a prior grant.
Trupanion, Inc. Chief Legal Officer Asher Bearman reported routine equity compensation activity involving restricted stock units (RSUs) and related tax withholding. On May 22, 2026 and May 25, 2026, RSUs converted into common stock and the company withheld shares to cover income tax obligations.
Across these transactions, Bearman acquired 2,609 shares of common stock through RSU vesting and 844 shares were withheld by the issuer to satisfy tax withholding and remittance obligations, which the filing notes does not represent a sale by the reporting person. Following the latest transaction, Bearman directly owns 72,244 shares of Trupanion common stock.
Morgan Stanley Smith Barney LLC filed a Form 144 reporting a proposed sale of 6,177 shares of common stock. The notice lists 3,340 restricted shares dated 05/22/2026 and 2,837 restricted shares dated 05/25/2026. The form lists the transaction date 05/27/2026 and identifies the securities as restricted stock.