Welcome to our dedicated page for Trupanion SEC filings (Ticker: TRUP), a comprehensive resource for investors and traders seeking official regulatory documents including 10-K annual reports, 10-Q quarterly earnings, 8-K material events, and insider trading forms.
Trupanion, Inc. filings document the company’s pet medical insurance business, public-company governance, and capital structure. Form 8-K reports include quarterly and annual operating results, with disclosures on subscription revenue, enrolled pets, net acquisition cost, adjusted EBITDA, operating cash flow, and other measures used to describe the company’s insurance economics.
The filing record also covers material agreements, including credit facilities, secured borrowings, maturity terms, covenants, and limits on corporate actions. Proxy materials document director elections, board composition, executive compensation, equity awards, shareholder voting matters, and related governance disclosures.
TRUPANION, INC. executive Simon Wheeler, EVP Trupanion International, exercised 1,526 restricted stock units into common stock on February 22, 2026 as part of his equity compensation. These RSUs came from a grant of 12,203 units awarded on February 27, 2024 that vests in eighths starting May 22, 2024 and then quarterly.
The amended Form 4 also corrects earlier clerical errors in reported derivative holdings for this RSU award, clarifying that 1,526 RSUs were beneficially owned as of November 25, 2025 and zero RSUs remained as of February 24, 2026. The filing reflects routine compensation-related vesting rather than an open-market trade.
Trupanion, Inc. executive Simon Wheeler reported an amendment to prior insider filings and a routine equity vesting. On May 22, 2026, he exercised 937 restricted stock units, which converted into 937 shares of common stock at a price of $0.00 per share. Following this transaction, he directly held 6,563 shares of common stock.
The amendment also corrects previously reported holdings for a 15,000-unit RSU grant made on February 27, 2024. The corrected derivative amounts beneficially owned were 8,438 units as of November 25, 2025, 7,500 units as of February 24, 2026, and 6,563 units as of May 27, 2026.
TRUPANION, INC. Chief Operating Officer John R. Gallagher reported an open-market sale of 3,603 shares of common stock on May 28, 2026 at a weighted average price of $21.6912 per share. Following the transaction, he directly holds 33,065 shares.
The sale was executed under a pre-arranged Rule 10b5-1 trading plan adopted on August 20, 2025, meaning Gallagher had no discretion over the timing. The shares were sold in multiple trades at prices ranging from $21.220 to $22.085 per share.
TRUP discloses a Form 144 notice reporting proposed and recent sales of Common stock. The filing lists 3,603 shares of restricted Common stock as the securities to be sold and shows recent dispositions by John Gallagher: 431 shares on 04/28/2026 for $11,839.57 and 430 shares on 03/30/2026 for $10,952.10. The broker/filing agent is noted as Morgan Stanley Smith Barney LLC.
TRUPANION, INC. executive Simon Wheeler, EVP Trupanion International, reported routine equity compensation activity involving restricted stock units (RSUs) that convert into common stock on a one-for-one basis. On May 22 and May 25, 2026, RSUs vested and were exercised into a total of 2,169 shares of common stock through multiple transactions coded "M" for derivative exercises.
In connection with these vestings, 1,017 common shares coded "F" were withheld by the issuer at prices of $21.98 and $21.86 per share to satisfy income tax withholding and remittance obligations, which the filing explicitly states do not represent sales by Wheeler. After these transactions, Wheeler directly owned 24,389 shares of common stock, and still held RSU awards originally granted on August 14, 2023, February 27, 2024, February 27, 2025, and February 20, 2026 that continue to vest over time, subject to continued service.
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.