Every Form 4 that Trupanion (TRUP) has filed with the SEC in the last 12 months is listed below, newest first, and each one links through to the document itself with the summary and the scores our analysis gives it.
A Form 4 covers the transactions officers, directors and large holders report, so if you follow TRUP and want that one kind of document rather than the whole filing history, this is the page to keep. The company's other filings, of every form, are on the full TRUP filings page.
TRUPANION, INC. (TRUP) reported that Chief Operating Officer John R. Gallagher sold 3,604 shares of common stock on August 28, 2026 at $29.70 per share in an open-market or private transaction. Following the sale, he directly holds 33,742 shares. The transaction was executed under a pre-arranged Rule 10b5-1 trading plan, under which he had no discretion over timing.
TRUPANION, INC. (TRUP) director Howard E. Rubin reported equity-compensation activity involving restricted stock units and common stock. On August 22, 2026, three blocks of 140 RSUs each, covering 140 shares of common stock per block, were reported as derivative dispositions, while corresponding three acquisitions of 140 common shares each were reported as exercises/conversions. Footnotes state the RSUs convert into common stock on a one-for-one basis and vest in quarterly installments through May 22, 2027, in connection with Rubin’s service on boards of wholly owned subsidiaries.
TRUPANION, INC. (TRUP) director Bradley S. Powell reported the vesting and conversion of 1,640 Restricted Stock Units into common stock on a one-for-one basis. This RSU conversion resulted in an acquisition of 1,640 shares of common stock, bringing his directly held common stock to 3,546 shares, with 4,923 RSUs remaining outstanding that continue to vest through May 22, 2027, subject to continued service.
TRUPANION, INC. (TRUP) reported that Chief Legal Officer Asher Bearman had multiple restricted stock unit (RSU) awards vest on August 22 and 25, 2026, converting an aggregate 2,610 RSUs into an equal number of shares of common stock.
In connection with these vestings, a total of 841 shares of common stock were withheld by the issuer to satisfy income tax withholding obligations at prices of about $31.76–$31.84 per share, which the company specifies do not represent market sales by the reporting person.
TRUPANION, INC. (TRUP) reported that executive officer Steve Weinrauch, EVP, North America & Vet Strategy, exercised previously granted restricted stock units (RSUs) into a total of 4,859 shares of common stock on August 22 and 25, 2026. The RSUs convert into common shares on a one-for-one basis. In connection with these vestings, a total of 1,181 common shares were delivered or withheld to satisfy income tax withholding and remittance obligations, which the company notes do not represent sales by the reporting person.
TRUPANION, INC. (TRUP) reported that Chief Administration Officer Brenna McGibney had restricted stock units vest on August 22 and 25, 2026, converting a total of 6,430 RSUs into common stock. To cover income tax withholding, the issuer withheld 3,438 common shares at prices of $31.76 and $31.84 per share, which the company states do not represent a sale by McGibney. All transactions were non‑open‑market RSU vesting, with no reported discretionary share sales.
TRUPANION, INC. (TRUP) reported that executive vice president Simon Wheeler had restricted stock units vest and convert into common stock on August 22 and 25, 2026. In total, 2,173 RSUs were exercised into an equal number of common shares, and 1,085 shares were withheld by the issuer to satisfy income tax withholding and remittance obligations. Footnotes state these withholdings do not represent sales by the reporting person.
TRUPANION, INC. (TRUP) Chief Financial Officer Fawwad Qureshi reported multiple equity transactions. On 2026-08-26, he sold 6,111 shares of common stock in open-market or private transactions at a weighted average price of $30.01 per share. Around 2026-08-22 and 2026-08-25, a total of 13,746 restricted stock units (RSUs) converted into an equal number of common shares, while 5,486 shares were withheld by the issuer at prices around $31.76–$31.84 per share solely to satisfy income tax withholding and remittance obligations, which the company states do not represent sales by Qureshi.
TRUPANION, INC. (TRUP) CEO and director Margaret Tooth reported multiple equity compensation transactions. On August 22 and 25, 2026 she exercised and vested 19,042 RSUs into the same number of common shares. Of these, 7,000 shares were withheld by the issuer to cover income tax obligations and 491 shares were sold in a market transaction at $31.84 per share. The remaining shares from these RSU conversions increased her directly held common stock, although post-transaction holdings are not stated here.
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. 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. 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. Chief Operating Officer John R. Gallagher reported an open-market sale of 431 shares of Common Stock at $25.35 per share. After this transaction, he directly holds 32,634 shares. The sale was executed under a pre-arranged Rule 10b5-1 trading plan, which set the timing in advance.
TRUPANION, INC. executive Steve Weinrauch, EVP North America & Vet Strategy, reported an exercise-and-sell transaction in company stock. He sold 6,674 shares of common stock in an open-market sale at a weighted average price of $22.00 per share, with individual trades ranging from $21.95 to $22.04.
On the same date, he exercised 8,500 stock options with a $15.46 exercise price, converting them into common shares and fully exhausting that option grant. Following these transactions, Weinrauch directly owns 78,062 shares of Trupanion common stock.
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.
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 24,239 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.
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.
Trupanion director Elizabeth McLaughlin received a new equity award in the form of restricted stock units. On May 11, 2026, she was granted 3,281 RSUs, each convertible into one share of Trupanion common stock.
The RSUs vest in four equal installments, with one-quarter of the units converting into common stock on each of August 22, 2026, November 22, 2026, February 22, 2027, and May 22, 2027, as long as she continues to serve through each vesting date. She has elected deferred settlement so the award will not actually settle into shares until 60 days after her death, disability, or separation from service, or immediately if there is a change of control.
TRUPANION, INC. director Bradley S. Powell reported a grant of 6,563 restricted stock units (RSUs) linked to the company’s common stock. These RSUs were awarded at no cash cost to Powell and convert into common shares on a one-for-one basis as they vest.
The RSUs vest in four equal installments: one‑quarter of the award on each of August 22, 2026, November 22, 2026, February 22, 2027, and May 22, 2027, subject to Powell’s continued service through each vesting date. After this grant, Powell’s reported RSU holdings from this award total 6,563 units.
TRUPANION, INC. director Max Broden received a grant of 6,375 restricted stock units (RSUs) on May 11, 2026. These RSUs convert into common stock on a one-for-one basis and represent his reported derivative holdings following the transaction.
The award is scheduled to vest in four equal installments, each covering 1/4 of the total shares, on August 22, 2026, November 22, 2026, February 22, 2027, and May 22, 2027, subject to his continued service. Because Broden will not stand for reelection at the 2026 Annual Meeting of Stockholders, he will vest in 1/4 of the shares immediately prior to that meeting if he remains in service, and the remaining unvested shares will be forfeited under the Non-Employee Director Compensation Program.
The reporting person has elected deferred settlement, so the vested RSUs will generally not settle into common stock until 60 days after his death, disability or separation from service, or immediately upon a change of control.
TRUPANION, INC. director Paulette R. Dodson received a grant of 4,031 restricted stock units (RSUs) on May 11, 2026 as equity compensation. These RSUs convert into common stock on a one-for-one basis.
The award vests in four equal installments, with one quarter of the RSUs scheduled to vest on each of August 22, 2026, November 22, 2026, February 22, 2027, and May 22, 2027, subject to continued service. Settlement is deferred until 60 days after Dodson’s death, disability, or separation from service, or immediately upon a change of control.
TRUPANION, INC. director Howard E. Rubin received equity compensation in the form of restricted stock units. On May 11, 2026, he was granted three separate awards of 562 RSUs each, for a total of 1,686 RSUs, in connection with his service on the boards of wholly-owned subsidiaries.
The RSUs convert into Trupanion common stock on a one-for-one basis. They vest in four equal installments, with one quarter of the total shares vesting on each of August 22, 2026, November 22, 2026, February 22, 2027, and May 22, 2027, provided Rubin continues his service through each vesting date.
TRUPANION, INC. director Darryl Rawlings reported an internal restructuring-related transaction involving indirectly held common stock. On May 6, 2026, Kuyashii Primary Equities LLC, an entity associated with him, received 1,359 shares after an event of default on a secured loan with stock pledged as collateral. Following this collateral delivery, Kuyashii Primary Equities LLC is shown as beneficially owning 1,435,340 shares of Trupanion common stock indirectly held for Rawlings.
TRUPANION, INC. Chief Operating Officer John R. Gallagher executed an open-market sale of 431 shares of common stock at $27.47 per share. This transaction was carried out under a pre-arranged Rule 10b5-1 trading plan, meaning the timing was predetermined. Following the sale, Gallagher directly holds 31,526 shares of Trupanion common stock.
TRUPANION, INC. Chief Operating Officer John R. Gallagher executed an open-market sale of 430 shares of common stock at $25.47 per share on March 30, 2026, under a pre-established Rule 10b5-1 trading plan. He continues to hold 31,957 shares directly after this transaction.
TRUPANION, INC. Chief Revenue Officer Emily Dreyer reported an open-market sale of company stock. On March 4, 2026, she sold 7,792 shares of common stock at an average price of $28.1468 per share. After this transaction, she directly owned 35,627 common shares.
Trupanion, Inc. Chief Financial Officer Fawwad Qureshi reported an open-market sale of 2,837 shares of common stock on February 27, 2026, at a weighted average price of $26.4629 per share. The sale was executed under a pre-arranged Rule 10b5-1 trading plan adopted on May 19, 2025, and left him with no directly held shares reported after the transaction.
TRUPANION, INC. Chief Operating Officer John R. Gallagher reported an open-market sale of 5,283 shares of common stock on February 27, 2026, at a weighted average price of $26.5153 per share. Following this transaction, he directly owned 32,387 shares.
The sale was executed under a pre-established Rule 10b5-1 trading plan adopted on August 20, 2025, as part of a plan of financial diversification, meaning Gallagher had no discretion over the timing. The weighted average price reflects multiple trades between $26.08 and $26.84 per share.
Trupanion, Inc. CEO Margaret Tooth reported routine equity compensation activity involving restricted stock units (RSUs) and related tax withholding. On February 25, 2026, RSUs converted into 3,266 and 1,250 shares of common stock on a one-for-one basis, reflecting previously granted awards.
To cover income tax obligations from these vestings, the company withheld 1,285 and 491 common shares at $26.70 per share, which the disclosure states does not represent a sale by the CEO. Following these transactions, Margaret Tooth directly owned 164,829 Trupanion common shares.
Trupanion, Inc. Chief Administration Officer Brenna McGibney reported RSU vesting and related share movements. On February 25, 2026, she acquired 646 shares of common stock through the conversion of restricted stock units at $0.00 per share.
To cover income tax withholding on this vesting, a total of 343 common shares were disposed of at $26.70 per share, as disclosed as a tax-withholding disposition rather than an open-market sale. After these transactions, she directly owned 8,453 shares of Trupanion common stock.
TRUPANION, INC. director Darryl Rawlings exercised previously granted restricted stock units, converting them into common shares. On February 25, 2026, 946 RSUs were exercised at a price of $0.00 per unit and converted into 946 shares of common stock on a one-for-one basis. Following this non-cash derivative conversion, Rawlings directly owned 42,232 shares of Trupanion common stock.
Trupanion, Inc. Chief Financial Officer Fawwad Qureshi reported multiple share transactions involving common stock and restricted stock units. On February 25, 2026, he exercised 3,750 restricted stock units that convert into common stock on a one-for-one basis and received 3,750 common shares.
On the same date, he sold 4,645 common shares in an open-market transaction at a weighted average price of $25.61 per share, under a pre-arranged Rule 10b5-1 trading plan adopted on May 19, 2025, meaning he had no discretion over timing. The weighted average sale price reflects multiple trades between $25.35 and $25.89 per share.
In addition, 913 common shares were withheld by the company at $26.70 per share to cover income tax obligations on the RSU vesting, which is described as not representing a sale. After these transactions, he directly owned 2,837 common shares and 26,250 RSUs.
TRUPANION, INC. executive Simon Wheeler, EVP, Trupanion International, reported routine equity compensation activity involving restricted stock units and common shares. On February 25, 2026, 322 restricted stock units were exercised and converted into 322 shares of common stock at a price of $0.00 per share.
Following this conversion, Wheeler directly owned 23,238 shares of common stock before a portion was withheld for taxes. Separately, 151 common shares were disposed of at $26.70 per share to satisfy income tax withholding and remittance obligations tied to the RSU vesting, leaving Wheeler with 23,087 directly owned common shares. Footnotes clarify this tax-related disposition does not represent an open-market sale by Wheeler.
TRUPANION, INC. Chief Legal Officer Asher Bearman reported routine equity compensation activity involving restricted stock units that convert into common stock on a one-for-one basis. On February 25, 2026, RSU conversions delivered 180 and 125 common shares at a stated price of $0.00 per share.
To satisfy income tax withholding tied to these vestings, the company withheld 68 and 48 common shares at $26.70 per share, which footnotes state do not represent sales by the insider. Following these transactions, Bearman directly owned 70,479 shares of Trupanion common stock.
TRUPANION, INC. Chief Operating Officer John R. Gallagher reported routine equity compensation activity involving restricted stock units that vested and converted into common stock. On February 25, 2026, RSUs converted into common shares on a one-for-one basis at no exercise price.
Gallagher acquired common stock through derivative exercises and had a portion of the newly vested shares withheld by the company to cover income tax obligations at a price of $26.70 per share, which the footnotes clarify does not represent an open-market sale. After these transactions, he directly held 37,670 shares of common stock.
Trupanion, Inc. Chief Revenue Officer Emily Dreyer reported routine equity activity linked to restricted stock units (RSUs). On February 25, 2026, RSUs covering 1,482 and 343 units converted into the same number of common shares on a one-for-one basis.
To cover income tax withholding on these vestings, 360 and 83 common shares were withheld by Trupanion at a price of $26.70 per share, which the footnotes state does not represent a sale by Dreyer. After these transactions, Dreyer directly owned 43,419 common shares.
TRUPANION, INC. executive Steve Weinrauch, EVP North America & Vet Strategy, reported multiple equity transactions on February 25, 2026 linked to previously granted restricted stock units (RSUs). Several RSU awards vested and converted into common stock on a one-for-one basis, increasing his direct holdings.
In connection with these vestings, the issuer withheld 129 and 9 shares of common stock at $26.70 per share to satisfy income tax withholding and remittance obligations, which the disclosure states do not represent sales by Weinrauch. He also completed an open-market or private sale of 85 common shares at $26.70 per share. Following these transactions, he directly owned 72,559 shares of Trupanion common stock.
TRUPANION, INC. Chief Administration Officer Brenna McGibney reported equity compensation activity, including a new award and vesting of existing restricted stock units. On February 20, 2026, she received a grant of 21,212 restricted stock units (RSUs) that will vest in eighths starting May 22, 2026, then quarterly.
On February 22, 2026, multiple RSU tranches vested and converted into common stock on a one-for-one basis, increasing her direct common stock holdings through derivative exercises. On the same date, 699, 724, and 1,007 common shares were withheld at $27.16 per share to satisfy tax obligations, which the disclosure states does not represent a sale by the reporting person. After these transactions, she directly held 8,150 shares of common stock.
TRUPANION, INC. executive Steve Weinrauch, EVP North America & Vet Strategy, reported multiple equity compensation moves. On February 20, 2026, he was granted 12,260 restricted stock units (RSUs), which convert into common stock on a one-for-one basis and vest in eighths starting May 22, 2026, then quarterly, subject to continued service.
On February 22, 2026, previously granted RSUs were exercised and converted into 2,932 and 2,029 shares of common stock. To cover income tax withholding related to these vestings, 869 and 601 shares of common stock were withheld by the company at $27.16 per share, which the filing notes does not represent a sale by Weinrauch. After these transactions, he directly held 71,857 shares of common stock and 12,260 RSUs.