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TRUPANION, INC. (TRUP) reported Form 4 activity by Chief Operating Officer John R. Gallagher. On August 22 and 25, 2026, Gallagher exercised restricted stock units (RSUs) into common stock and had a portion of the resulting shares withheld by the issuer to cover income tax obligations. Footnotes state these withheld shares represent tax withholding and remittance, not market sales by Gallagher, and overall activity reflects RSU vesting rather than open-market trading.
TRUPANION, INC. (TRUP) director Darryl Rawlings reported an automatic conversion of 313 Restricted Stock Units (RSUs) into 313 shares of common stock on 2026-08-22. Following the transactions, he holds 1,875 RSUs and 25,151 common shares directly. The RSUs were part of a 5,000-unit grant awarded on 2024-02-27 that vests as to one-quarter on 2025-02-22 and then one-sixteenth of the total grant quarterly, subject to continued service through each vesting date.
TRUPANION, INC. (TRUP) received a Rule 144 notice from officer Fawwad Qureshi covering a proposed sale of company common stock. The notice reports an intent to sell 6,111 shares of TRUP common stock, with an indicated aggregate market value of $183,372.78, through Morgan Stanley Smith Barney LLC on or after 08/26/2026.
The shares to be sold were acquired as restricted stock from the issuer, vesting during the period 08/22/2026 through 08/25/2026. The filing also notes that Qureshi sold 6,177 shares of TRUP common stock in the prior three months on 05/27/2026 for an aggregate sale price of $136,938.53.
TRUPANION, INC. CEO and director Margaret Tooth reported a sale of 978 shares of Common Stock on August 11, 2026 at $29.05 per share. After this transaction, she directly held 175,401 shares. The sale was effected under a Rule 10b5-1(c) trading plan adopted on May 11, 2026, under which she had no discretion over trade timing and which was described as part of a plan of financial diversification.
Trupanion, Inc. shareholder Margaret R. Tooth filed a notice of intention to sell common stock. The planned sale covers 978 shares of common stock through Morgan Stanley Smith Barney LLC Executive Financial Services, with an aggregate market value of $28,410.90, to be sold on or after August 11, 2026 on NASDAQ. The disclosure also lists prior restricted stock awards and notes that 491 shares of common stock were sold for $10,733.26 on May 25, 2026.
Trupanion, Inc. reported an initial statement of beneficial ownership for Chief Marketing Officer Katherine Seawell. The Form 3 lists her as an officer but does not report any equity transactions or derivative positions in this filing.
Trupanion, Inc. reported Q2 2026 revenue of 392,934 (in thousands), up 11% year over year, with subscription revenue of 276,690 (in thousands) and other business revenue of 116,244 (in thousands). Subscription pets enrolled grew 5% to 1,124,548, while total pets enrolled declined 2% to 1,633,131 as lower-margin other business contracts ran off.
Operating income rose to 6,376 (in thousands) from 2,314 (in thousands), while net income was 6,831 (in thousands) versus 9,413 (in thousands) due to a prior-year nonmonetary exchange gain. For the first six months, revenue increased 12% to 776,983 (in thousands) and net income to 11,711 (in thousands). Monthly average revenue per subscription pet increased to 87.44 from 79.93, with average monthly retention at 98.37% and average pet acquisition cost rising to 299 from 276.
Cash, cash equivalents and restricted cash totaled 178,299 (in thousands) at June 30, 2026, alongside short-term investments of 249,131 (in thousands) and operating cash flow of 35,578 (in thousands) for the first half. Total principal on long-term debt was 107,500 (in thousands) under the PNC Facility. The board approved a new share repurchase program authorizing up to $100.0 million of common stock repurchases.
Trupanion reported second-quarter 2026 results with total revenue of $392.9 million, up 11% from a year earlier. Subscription business revenue grew to $276.7 million, up 14%. Total enrolled pets were 1,633,131, down 2%, while subscription pets rose 5% to 1,124,548.
GAAP net income for the quarter was $6.8 million, or $0.16 per basic and diluted share, compared with $9.4 million and $0.22 a year ago. Adjusted EBITDA increased to $19.8 million from $16.6 million. Operating cash flow was $21.0 million and free cash flow was $19.2 million, both higher than the prior year.
For the first six months of 2026, revenue was $777.0 million, up 12%, and net income was $11.7 million versus $7.9 million. Adjusted EBITDA was $37.1 million. At June 30, 2026, Trupanion held $398.5 million in cash and short-term investments and had $3.5 million available under its credit facility. In July 2026, an extraordinary $44 million dividend from its insurance subsidiary was approved, and the board authorized a share repurchase program of up to $100.0 million in common stock with no expiration, subject to factors including liquidity, credit facility compliance and market conditions.
TRUPANION, INC. Chief Operating Officer John R. Gallagher reported selling 431 shares of common stock on July 28, 2026 at $25.08 per share in an open-market transaction. After this sale, he directly holds 32,203 shares. The sale was executed under a pre-arranged Rule 10b5-1 trading plan adopted on August 20, 2025, which limited his discretion over timing.
Trupanion, Inc. insider John Gallagher filed to sell common stock under a planned transaction. The filing lists 431 shares of common stock to be sold through Morgan Stanley Smith Barney LLC Executive Financial Services on NASDAQ, with an intended sale date of July 28, 2026.
The filing also reports prior sales of Trupanion common stock over the past three months, including 3,603 shares for $78,153.39 on May 28, 2026 and 431 shares for $10,925.85 on June 29, 2026. It references restricted stock positions dated August 25, 2023 and November 25, 2023.