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GALLAGHER JOHN R

Disclosed activity across 1 company

Tapewire entity
17885
SEC CIK
0001967117

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Reported relationships

Latest disclosed role at each company.

CompanyLast reported asReport datePublished
TRUPANION, INC.TRUP · Entity 4822Chief Operating OfficerSeptember 28, 2026September 30, 2026

Disclosed balances

About these balances

Latest available filing per company, not a reconstructed current portfolio. Matching sequences show the last reported balance with all source rows expandable; grouping alone does not establish account ownership. Do not add unresolved positions together. Filings may omit unchanged positions, and amendments may correct only part of an older disclosure. Jointly reported shares are not necessarily this owner's personal holdings.

TRUPANION, INC.

Report date September 28, 2026 · Filed September 30, 2026

Security / awardOwnership accountDisclosed shares / unitsDisclosure context
Common StockSEC Table I · non-derivativeDirect33,311 Reported balance After 2026-09-28 transaction · row 1
1 source row

Row 1 · 2026-09-28 · Sale · Disposed 431 · Balance 33,311

F1: The exercise and sale reported were effected pursuant to a Rule 10b5-1 trading plan adopted by reporting person on August 20, 2025, in order to implement a plan of financial diversification. Accordingly, the reporting person had no discretion with regard to the timing of the transaction.

Filing footnotes · ownership attribution and instrument terms

F1: The exercise and sale reported were effected pursuant to a Rule 10b5-1 trading plan adopted by reporting person on August 20, 2025, in order to implement a plan of financial diversification. Accordingly, the reporting person had no discretion with regard to the timing of the transaction.

Transaction history

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Purchases/sales include open-market and private transactions. Plan disclosure applies to the filing; individual rows may differ. “Not disclosed” is not “unplanned.”

The cutoff filters transaction history only. Company summaries and owner relationships show the latest available disclosures. Parser corrections can improve historical records.

Transaction dateCompanyActivity / securityShares / unitsReported priceReported valueDetails
September 28, 2026 Filed Sep 30, 2026 22:53 UTC TRUPANION, INC. TRUP · Entity 4822 SaleCommon Stock 431 $22.92 $9,878.52
Disclosure

SEC source: 0001371285-26-000203 · wk-form4_1790808805.xml · nonDerivative · entry 1

GALLAGHER JOHN R · CIK 0001967117 · Chief Operating Officer

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 33,311

F1 · shares: The exercise and sale reported were effected pursuant to a Rule 10b5-1 trading plan adopted by reporting person on August 20, 2025, in order to implement a plan of financial diversification. Accordingly, the reporting person had no discretion with regard to the timing of the transaction.

Read SEC document
August 28, 2026 Filed Sep 1, 2026 23:37 UTC TRUPANION, INC. TRUP · Entity 4822 SaleCommon Stock 3,604 $29.70 $107,038.80
Disclosure

SEC source: 0001371285-26-000199 · wk-form4_1788305832.xml · nonDerivative · entry 1

GALLAGHER JOHN R · CIK 0001967117 · Chief Operating Officer

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 33,742

F1 · shares: The exercise and sale reported were effected pursuant to a Rule 10b5-1 trading plan adopted by reporting person on August 20, 2025, in order to implement a plan of financial diversification. Accordingly, the reporting person had no discretion with regard to the timing of the transaction.

Read SEC document
August 25, 2026 Filed Aug 26, 2026 22:56 UTC TRUPANION, INC. TRUP · Entity 4822 Exercise / conversionRestricted Stock Unit (RSU) · Derivative 45 $0.00 $0.00
Disclosure

SEC source: 0001371285-26-000189 · wk-form4_1787784974.xml · derivative · entry 18

GALLAGHER JOHN R · CIK 0001967117 · Chief Operating Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 180

Underlying: Common Stock · 45 shares

Expires 2027-08-25

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · derivative.exercise_price: Restricted stock units convert into common stock on a one-for-one basis.

F8 · derivative.exercise_date: On August 14, 2023, the reporting person was granted 721 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.

F8 · derivative.expiration_date: On August 14, 2023, the reporting person was granted 721 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.

Read SEC document
August 25, 2026 Filed Aug 26, 2026 22:56 UTC TRUPANION, INC. TRUP · Entity 4822 Exercise / conversionRestricted Stock Unit (RSU) · Derivative 452 $0.00 $0.00
Disclosure

SEC source: 0001371285-26-000189 · wk-form4_1787784974.xml · derivative · entry 17

GALLAGHER JOHN R · CIK 0001967117 · Chief Operating Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 1,806

Underlying: Common Stock · 452 shares

Expires 2027-08-25

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · derivative.exercise_price: Restricted stock units convert into common stock on a one-for-one basis.

F7 · derivative.exercise_date: On August 14, 2023, the reporting person was granted 7,223 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.

F7 · derivative.expiration_date: On August 14, 2023, the reporting person was granted 7,223 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.

Read SEC document
August 25, 2026 Filed Aug 26, 2026 22:56 UTC TRUPANION, INC. TRUP · Entity 4822 Exercise / conversionRestricted Stock Unit (RSU) · Derivative 28 $0.00 $0.00
Disclosure

SEC source: 0001371285-26-000189 · wk-form4_1787784974.xml · derivative · entry 16

GALLAGHER JOHN R · CIK 0001967117 · Chief Operating Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 87

Underlying: Common Stock · 28 shares

Expires 2027-05-25

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · derivative.exercise_price: Restricted stock units convert into common stock on a one-for-one basis.

F6 · derivative.exercise_date: On May 15, 2023, the reporting person was granted 460 restricted stock units (RSUs). The RSUs vested and converted into common stock of the Issuer as to 1/4th of the total shares on May 25, 2024, after which 1/16th of the total shares vest quarterly, subject to continued service through each vest date.

F6 · derivative.expiration_date: On May 15, 2023, the reporting person was granted 460 restricted stock units (RSUs). The RSUs vested and converted into common stock of the Issuer as to 1/4th of the total shares on May 25, 2024, after which 1/16th of the total shares vest quarterly, subject to continued service through each vest date.

Read SEC document
August 25, 2026 Filed Aug 26, 2026 22:56 UTC TRUPANION, INC. TRUP · Entity 4822 Tax withholdingCommon Stock 10 $31.84 $318.40
Disclosure

SEC source: 0001371285-26-000189 · wk-form4_1787784974.xml · nonDerivative · entry 12

GALLAGHER JOHN R · CIK 0001967117 · Chief Operating Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 37,346

F2 · shares: 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.

Read SEC document
August 25, 2026 Filed Aug 26, 2026 22:56 UTC TRUPANION, INC. TRUP · Entity 4822 Exercise / conversionCommon Stock 45 Not disclosed Not disclosed
Disclosure

SEC source: 0001371285-26-000189 · wk-form4_1787784974.xml · nonDerivative · entry 11

GALLAGHER JOHN R · CIK 0001967117 · Chief Operating Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 37,356

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · price: Restricted stock units convert into common stock on a one-for-one basis.

Read SEC document
August 25, 2026 Filed Aug 26, 2026 22:56 UTC TRUPANION, INC. TRUP · Entity 4822 Tax withholdingCommon Stock 110 $31.84 $3,502.40
Disclosure

SEC source: 0001371285-26-000189 · wk-form4_1787784974.xml · nonDerivative · entry 10

GALLAGHER JOHN R · CIK 0001967117 · Chief Operating Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 37,311

F2 · shares: 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.

Read SEC document
August 25, 2026 Filed Aug 26, 2026 22:56 UTC TRUPANION, INC. TRUP · Entity 4822 Exercise / conversionCommon Stock 452 Not disclosed Not disclosed
Disclosure

SEC source: 0001371285-26-000189 · wk-form4_1787784974.xml · nonDerivative · entry 9

GALLAGHER JOHN R · CIK 0001967117 · Chief Operating Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 37,421

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · price: Restricted stock units convert into common stock on a one-for-one basis.

Read SEC document
August 25, 2026 Filed Aug 26, 2026 22:56 UTC TRUPANION, INC. TRUP · Entity 4822 Tax withholdingCommon Stock 6 $31.84 $191.04
Disclosure

SEC source: 0001371285-26-000189 · wk-form4_1787784974.xml · nonDerivative · entry 8

GALLAGHER JOHN R · CIK 0001967117 · Chief Operating Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 36,969

F2 · shares: 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.

Read SEC document
August 25, 2026 Filed Aug 26, 2026 22:56 UTC TRUPANION, INC. TRUP · Entity 4822 Exercise / conversionCommon Stock 28 Not disclosed Not disclosed
Disclosure

SEC source: 0001371285-26-000189 · wk-form4_1787784974.xml · nonDerivative · entry 7

GALLAGHER JOHN R · CIK 0001967117 · Chief Operating Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 36,975

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · price: Restricted stock units convert into common stock on a one-for-one basis.

Read SEC document
August 22, 2026 Filed Aug 26, 2026 22:56 UTC TRUPANION, INC. TRUP · Entity 4822 Exercise / conversionRestricted Stock Unit (RSU) · Derivative 2,076 $0.00 $0.00
Disclosure

SEC source: 0001371285-26-000189 · wk-form4_1787784974.xml · derivative · entry 15

GALLAGHER JOHN R · CIK 0001967117 · Chief Operating Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 12,457

Underlying: Common Stock · 2,076 shares

Expires 2028-02-22

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · derivative.exercise_price: Restricted stock units convert into common stock on a one-for-one basis.

F5 · derivative.exercise_date: On February 20, 2026, the reporting person was granted 16,609 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.

F5 · derivative.expiration_date: On February 20, 2026, the reporting person was granted 16,609 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.

Read SEC document
August 22, 2026 Filed Aug 26, 2026 22:56 UTC TRUPANION, INC. TRUP · Entity 4822 Exercise / conversionRestricted Stock Unit (RSU) · Derivative 3,328 $0.00 $0.00
Disclosure

SEC source: 0001371285-26-000189 · wk-form4_1787784974.xml · derivative · entry 14

GALLAGHER JOHN R · CIK 0001967117 · Chief Operating Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 6,655

Underlying: Common Stock · 3,328 shares

Expires 2027-02-22

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · derivative.exercise_price: Restricted stock units convert into common stock on a one-for-one basis.

F4 · derivative.exercise_date: On February 27, 2025, the reporting person was granted 26,619 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.

F4 · derivative.expiration_date: On February 27, 2025, the reporting person was granted 26,619 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.

Read SEC document
August 22, 2026 Filed Aug 26, 2026 22:56 UTC TRUPANION, INC. TRUP · Entity 4822 Exercise / conversionRestricted Stock Unit (RSU) · Derivative 865 $0.00 $0.00
Disclosure

SEC source: 0001371285-26-000189 · wk-form4_1787784974.xml · derivative · entry 13

GALLAGHER JOHN R · CIK 0001967117 · Chief Operating Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 7,784

Underlying: Common Stock · 865 shares

Expires 2028-11-22

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · derivative.exercise_price: Restricted stock units convert into common stock on a one-for-one basis.

F3 · derivative.exercise_date: On November 12, 2024, the reporting person was granted 13,838 restricted stock units (RSUs). The RSUs vest and convert into common stock of the Issuer as to 1/4th of the total shares on November 22, 2025, after which 1/16th of the total shares vest quarterly, subject to continued service through each vest date.

F3 · derivative.expiration_date: On November 12, 2024, the reporting person was granted 13,838 restricted stock units (RSUs). The RSUs vest and convert into common stock of the Issuer as to 1/4th of the total shares on November 22, 2025, after which 1/16th of the total shares vest quarterly, subject to continued service through each vest date.

Read SEC document
August 22, 2026 Filed Aug 26, 2026 22:56 UTC TRUPANION, INC. TRUP · Entity 4822 Tax withholdingCommon Stock 505 $31.76 $16,038.80
Disclosure

SEC source: 0001371285-26-000189 · wk-form4_1787784974.xml · nonDerivative · entry 6

GALLAGHER JOHN R · CIK 0001967117 · Chief Operating Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 36,947

F2 · shares: 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.

Read SEC document
August 22, 2026 Filed Aug 26, 2026 22:56 UTC TRUPANION, INC. TRUP · Entity 4822 Exercise / conversionCommon Stock 2,076 Not disclosed Not disclosed
Disclosure

SEC source: 0001371285-26-000189 · wk-form4_1787784974.xml · nonDerivative · entry 5

GALLAGHER JOHN R · CIK 0001967117 · Chief Operating Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 37,452

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · price: Restricted stock units convert into common stock on a one-for-one basis.

Read SEC document
August 22, 2026 Filed Aug 26, 2026 22:56 UTC TRUPANION, INC. TRUP · Entity 4822 Tax withholdingCommon Stock 810 $31.76 $25,725.60
Disclosure

SEC source: 0001371285-26-000189 · wk-form4_1787784974.xml · nonDerivative · entry 4

GALLAGHER JOHN R · CIK 0001967117 · Chief Operating Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 35,376

F2 · shares: 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.

Read SEC document
August 22, 2026 Filed Aug 26, 2026 22:56 UTC TRUPANION, INC. TRUP · Entity 4822 Exercise / conversionCommon Stock 3,328 Not disclosed Not disclosed
Disclosure

SEC source: 0001371285-26-000189 · wk-form4_1787784974.xml · nonDerivative · entry 3

GALLAGHER JOHN R · CIK 0001967117 · Chief Operating Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 36,186

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · price: Restricted stock units convert into common stock on a one-for-one basis.

Read SEC document
August 22, 2026 Filed Aug 26, 2026 22:56 UTC TRUPANION, INC. TRUP · Entity 4822 Tax withholdingCommon Stock 210 $31.76 $6,669.60
Disclosure

SEC source: 0001371285-26-000189 · wk-form4_1787784974.xml · nonDerivative · entry 2

GALLAGHER JOHN R · CIK 0001967117 · Chief Operating Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 32,858

F2 · shares: 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.

Read SEC document
August 22, 2026 Filed Aug 26, 2026 22:56 UTC TRUPANION, INC. TRUP · Entity 4822 Exercise / conversionCommon Stock 865 Not disclosed Not disclosed
Disclosure

SEC source: 0001371285-26-000189 · wk-form4_1787784974.xml · nonDerivative · entry 1

GALLAGHER JOHN R · CIK 0001967117 · Chief Operating Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 33,068

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · price: Restricted stock units convert into common stock on a one-for-one basis.

Read SEC document
July 28, 2026 Filed Jul 30, 2026 21:44 UTC TRUPANION, INC. TRUP · Entity 4822 SaleCommon Stock 431 $25.08 $10,809.48
Disclosure

SEC source: 0001371285-26-000161 · wk-form4_1785447846.xml · nonDerivative · entry 1

GALLAGHER JOHN R · CIK 0001967117 · Chief Operating Officer

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 32,203

F1 · shares: The exercise and sale reported were effected pursuant to a Rule 10b5-1 trading plan adopted by reporting person on August 20, 2025, in order to implement a plan of financial diversification. Accordingly, the reporting person had no discretion with regard to the timing of the transaction.

Read SEC document
June 29, 2026 Filed Jul 1, 2026 23:09 UTC TRUPANION, INC. TRUP · Entity 4822 SaleCommon Stock 431 $25.35 $10,925.85
Disclosure

SEC source: 0001371285-26-000157 · wk-form4_1782947352.xml · nonDerivative · entry 1

GALLAGHER JOHN R · CIK 0001967117 · Chief Operating Officer

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 32,634

F1 · shares: The sale reported is effected pursuant to a Rule 10b5-1 trading plan adopted by reporting person on August 20, 2025, in order to implement a plan of financial diversification. Accordingly, the reporting person had no discretion with regard to the timing of the transaction.

Read SEC document
May 28, 2026 Filed Jun 2, 2026 00:34 UTC TRUPANION, INC. TRUP · Entity 4822 SaleCommon Stock 3,603 $21.69 $78,153.39
Disclosure

SEC source: 0001371285-26-000146 · wk-form4_1780360443.xml · nonDerivative · entry 1

GALLAGHER JOHN R · CIK 0001967117 · Chief Operating Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 33,065

F1 · shares: The sale reported is effected pursuant to a Rule 10b5-1 trading plan adopted by reporting person on August 20, 2025, in order to implement a plan of financial diversification. Accordingly, the reporting person had no discretion with regard to the timing of the transaction.

F2 · price: The reported price in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $21.220 to $22.085 per share, inclusive. The reporting person undertakes to provide to the issuer, any security holder of the issuer, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the range set forth in this footnote (2).

Read SEC document
May 25, 2026 Filed May 28, 2026 01:41 UTC TRUPANION, INC. TRUP · Entity 4822 Exercise / conversionRestricted Stock Unit (RSU) · Derivative 45 $0.00 $0.00
Disclosure

SEC source: 0001371285-26-000138 · wk-form4_1779932481.xml · derivative · entry 18

GALLAGHER JOHN R · CIK 0001967117 · Chief Operating Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 225

Underlying: Common Stock · 45 shares

Expires 2027-08-25

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · derivative.exercise_price: Restricted stock units convert into common stock on a one-for-one basis.

F8 · derivative.exercise_date: On August 14, 2023, the reporting person was granted 721 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.

F8 · derivative.expiration_date: On August 14, 2023, the reporting person was granted 721 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.

Read SEC document
May 25, 2026 Filed May 28, 2026 01:41 UTC TRUPANION, INC. TRUP · Entity 4822 Exercise / conversionRestricted Stock Unit (RSU) · Derivative 451 $0.00 $0.00
Disclosure

SEC source: 0001371285-26-000138 · wk-form4_1779932481.xml · derivative · entry 17

GALLAGHER JOHN R · CIK 0001967117 · Chief Operating Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 2,258

Underlying: Common Stock · 451 shares

Expires 2027-08-25

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · derivative.exercise_price: Restricted stock units convert into common stock on a one-for-one basis.

F7 · derivative.exercise_date: On August 14, 2023, the reporting person was granted 7,223 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.

F7 · derivative.expiration_date: On August 14, 2023, the reporting person was granted 7,223 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.

Read SEC document
May 25, 2026 Filed May 28, 2026 01:41 UTC TRUPANION, INC. TRUP · Entity 4822 Exercise / conversionRestricted Stock Unit (RSU) · Derivative 29 $0.00 $0.00
Disclosure

SEC source: 0001371285-26-000138 · wk-form4_1779932481.xml · derivative · entry 16

GALLAGHER JOHN R · CIK 0001967117 · Chief Operating Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 115

Underlying: Common Stock · 29 shares

Expires 2027-05-25

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · derivative.exercise_price: Restricted stock units convert into common stock on a one-for-one basis.

F6 · derivative.exercise_date: On May 15, 2023, the reporting person was granted 460 restricted stock units (RSUs). The RSUs vested and converted into common stock of the Issuer as to 1/4th of the total shares on May 25, 2024, after which 1/16th of the total shares vest quarterly, subject to continued service through each vest date.

F6 · derivative.expiration_date: On May 15, 2023, the reporting person was granted 460 restricted stock units (RSUs). The RSUs vested and converted into common stock of the Issuer as to 1/4th of the total shares on May 25, 2024, after which 1/16th of the total shares vest quarterly, subject to continued service through each vest date.

Read SEC document
May 25, 2026 Filed May 28, 2026 01:41 UTC TRUPANION, INC. TRUP · Entity 4822 Tax withholdingCommon Stock 10 $21.86 $218.60
Disclosure

SEC source: 0001371285-26-000138 · wk-form4_1779932481.xml · nonDerivative · entry 12

GALLAGHER JOHN R · CIK 0001967117 · Chief Operating Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 36,668

F2 · shares: 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.

Read SEC document
May 25, 2026 Filed May 28, 2026 01:41 UTC TRUPANION, INC. TRUP · Entity 4822 Exercise / conversionCommon Stock 45 Not disclosed Not disclosed
Disclosure

SEC source: 0001371285-26-000138 · wk-form4_1779932481.xml · nonDerivative · entry 11

GALLAGHER JOHN R · CIK 0001967117 · Chief Operating Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 36,678

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · price: Restricted stock units convert into common stock on a one-for-one basis.

Read SEC document
May 25, 2026 Filed May 28, 2026 01:41 UTC TRUPANION, INC. TRUP · Entity 4822 Tax withholdingCommon Stock 109 $21.86 $2,382.74
Disclosure

SEC source: 0001371285-26-000138 · wk-form4_1779932481.xml · nonDerivative · entry 10

GALLAGHER JOHN R · CIK 0001967117 · Chief Operating Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 36,633

F2 · shares: 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.

Read SEC document
May 25, 2026 Filed May 28, 2026 01:41 UTC TRUPANION, INC. TRUP · Entity 4822 Exercise / conversionCommon Stock 451 Not disclosed Not disclosed
Disclosure

SEC source: 0001371285-26-000138 · wk-form4_1779932481.xml · nonDerivative · entry 9

GALLAGHER JOHN R · CIK 0001967117 · Chief Operating Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 36,742

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · price: Restricted stock units convert into common stock on a one-for-one basis.

Read SEC document
May 25, 2026 Filed May 28, 2026 01:41 UTC TRUPANION, INC. TRUP · Entity 4822 Tax withholdingCommon Stock 7 $21.86 $153.02
Disclosure

SEC source: 0001371285-26-000138 · wk-form4_1779932481.xml · nonDerivative · entry 8

GALLAGHER JOHN R · CIK 0001967117 · Chief Operating Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 36,291

F2 · shares: 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.

Read SEC document
May 25, 2026 Filed May 28, 2026 01:41 UTC TRUPANION, INC. TRUP · Entity 4822 Exercise / conversionCommon Stock 29 Not disclosed Not disclosed
Disclosure

SEC source: 0001371285-26-000138 · wk-form4_1779932481.xml · nonDerivative · entry 7

GALLAGHER JOHN R · CIK 0001967117 · Chief Operating Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 36,298

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · price: Restricted stock units convert into common stock on a one-for-one basis.

Read SEC document
May 22, 2026 Filed May 28, 2026 01:41 UTC TRUPANION, INC. TRUP · Entity 4822 Exercise / conversionRestricted Stock Unit (RSU) · Derivative 2,076 $0.00 $0.00
Disclosure

SEC source: 0001371285-26-000138 · wk-form4_1779932481.xml · derivative · entry 15

GALLAGHER JOHN R · CIK 0001967117 · Chief Operating Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 14,533

Underlying: Common Stock · 2,076 shares

Expires 2028-02-22

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · derivative.exercise_price: Restricted stock units convert into common stock on a one-for-one basis.

F5 · derivative.exercise_date: On February 20, 2026, the reporting person was granted 16,609 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.

F5 · derivative.expiration_date: On February 20, 2026, the reporting person was granted 16,609 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.

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May 22, 2026 Filed May 28, 2026 01:41 UTC TRUPANION, INC. TRUP · Entity 4822 Exercise / conversionRestricted Stock Unit (RSU) · Derivative 3,327 $0.00 $0.00
Disclosure

SEC source: 0001371285-26-000138 · wk-form4_1779932481.xml · derivative · entry 14

GALLAGHER JOHN R · CIK 0001967117 · Chief Operating Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 9,983

Underlying: Common Stock · 3,327 shares

Expires 2027-02-22

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · derivative.exercise_price: Restricted stock units convert into common stock on a one-for-one basis.

F4 · derivative.exercise_date: On February 27, 2025, the reporting person was granted 26,619 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.

F4 · derivative.expiration_date: On February 27, 2025, the reporting person was granted 26,619 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.

Read SEC document
May 22, 2026 Filed May 28, 2026 01:41 UTC TRUPANION, INC. TRUP · Entity 4822 Exercise / conversionRestricted Stock Unit (RSU) · Derivative 865 $0.00 $0.00
Disclosure

SEC source: 0001371285-26-000138 · wk-form4_1779932481.xml · derivative · entry 13

GALLAGHER JOHN R · CIK 0001967117 · Chief Operating Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 8,649

Underlying: Common Stock · 865 shares

Expires 2028-11-22

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · derivative.exercise_price: Restricted stock units convert into common stock on a one-for-one basis.

F3 · derivative.exercise_date: On November 12, 2024, the reporting person was granted 13,838 restricted stock units (RSUs). The RSUs vest and convert into common stock of the Issuer as to 1/4th of the total shares on November 22, 2025, after which 1/16th of the total shares vest quarterly, subject to continued service through each vest date.

F3 · derivative.expiration_date: On November 12, 2024, the reporting person was granted 13,838 restricted stock units (RSUs). The RSUs vest and convert into common stock of the Issuer as to 1/4th of the total shares on November 22, 2025, after which 1/16th of the total shares vest quarterly, subject to continued service through each vest date.

Read SEC document
May 22, 2026 Filed May 28, 2026 01:41 UTC TRUPANION, INC. TRUP · Entity 4822 Tax withholdingCommon Stock 505 $21.98 $11,099.90
Disclosure

SEC source: 0001371285-26-000138 · wk-form4_1779932481.xml · nonDerivative · entry 6

GALLAGHER JOHN R · CIK 0001967117 · Chief Operating Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 36,269

F2 · shares: 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.

Read SEC document
May 22, 2026 Filed May 28, 2026 01:41 UTC TRUPANION, INC. TRUP · Entity 4822 Exercise / conversionCommon Stock 2,076 Not disclosed Not disclosed
Disclosure

SEC source: 0001371285-26-000138 · wk-form4_1779932481.xml · nonDerivative · entry 5

GALLAGHER JOHN R · CIK 0001967117 · Chief Operating Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 36,774

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · price: Restricted stock units convert into common stock on a one-for-one basis.

Read SEC document
May 22, 2026 Filed May 28, 2026 01:41 UTC TRUPANION, INC. TRUP · Entity 4822 Tax withholdingCommon Stock 810 $21.98 $17,803.80
Disclosure

SEC source: 0001371285-26-000138 · wk-form4_1779932481.xml · nonDerivative · entry 4

GALLAGHER JOHN R · CIK 0001967117 · Chief Operating Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 34,698

F2 · shares: 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.

Read SEC document
May 22, 2026 Filed May 28, 2026 01:41 UTC TRUPANION, INC. TRUP · Entity 4822 Exercise / conversionCommon Stock 3,327 Not disclosed Not disclosed
Disclosure

SEC source: 0001371285-26-000138 · wk-form4_1779932481.xml · nonDerivative · entry 3

GALLAGHER JOHN R · CIK 0001967117 · Chief Operating Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 35,508

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · price: Restricted stock units convert into common stock on a one-for-one basis.

Read SEC document
May 22, 2026 Filed May 28, 2026 01:41 UTC TRUPANION, INC. TRUP · Entity 4822 Tax withholdingCommon Stock 210 $21.98 $4,615.80
Disclosure

SEC source: 0001371285-26-000138 · wk-form4_1779932481.xml · nonDerivative · entry 2

GALLAGHER JOHN R · CIK 0001967117 · Chief Operating Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 32,181

F2 · shares: 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.

Read SEC document
May 22, 2026 Filed May 28, 2026 01:41 UTC TRUPANION, INC. TRUP · Entity 4822 Exercise / conversionCommon Stock 865 Not disclosed Not disclosed
Disclosure

SEC source: 0001371285-26-000138 · wk-form4_1779932481.xml · nonDerivative · entry 1

GALLAGHER JOHN R · CIK 0001967117 · Chief Operating Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 32,391

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · price: Restricted stock units convert into common stock on a one-for-one basis.

Read SEC document
April 28, 2026 Filed Apr 29, 2026 20:47 UTC TRUPANION, INC. TRUP · Entity 4822 SaleCommon Stock 431 $27.47 $11,839.57
Disclosure

SEC source: 0001371285-26-000087 · wk-form4_1777495640.xml · nonDerivative · entry 1

GALLAGHER JOHN R · CIK 0001967117 · Chief Operating Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 31,526

F1 · shares: The sale reported is effected pursuant to a Rule 10b5-1 trading plan adopted by reporting person on August 20, 2025, in order to implement a plan of financial diversification. Accordingly, the reporting person had no discretion with regard to the timing of the transaction.

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March 30, 2026 Filed Apr 2, 2026 00:33 UTC TRUPANION, INC. TRUP · Entity 4822 SaleCommon Stock 430 $25.47 $10,952.10
Disclosure

SEC source: 0001371285-26-000068 · wk-form4_1775090031.xml · nonDerivative · entry 1

GALLAGHER JOHN R · CIK 0001967117 · Chief Operating Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 31,957

F1 · shares: The sale reported is effected pursuant to a Rule 10b5-1 trading plan adopted by reporting person on August 20, 2025, in order to implement a plan of financial diversification. Accordingly, the reporting person had no discretion with regard to the timing of the transaction.

Read SEC document
February 27, 2026 Filed Mar 4, 2026 00:09 UTC TRUPANION, INC. TRUP · Entity 4822 SaleCommon Stock 5,283 $26.52 $140,080.33
Disclosure

SEC source: 0001371285-26-000063 · wk-form4_1772582982.xml · nonDerivative · entry 1

GALLAGHER JOHN R · CIK 0001967117 · Chief Operating Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 32,387

F1 · shares: The sale reported is effected pursuant to a Rule 10b5-1 trading plan adopted by reporting person on August 20, 2025, in order to implement a plan of financial diversification. Accordingly, the reporting person had no discretion with regard to the timing of the transaction.

F2 · price: The reported price in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $26.08 to $26.84 per share, inclusive. The reporting person undertakes to provide to the issuer, any security holder of the issuer, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the range set forth in this footnote (2).

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February 25, 2026 Filed Feb 28, 2026 01:02 UTC TRUPANION, INC. TRUP · Entity 4822 Exercise / conversionRestricted Stock Unit (RSU) · Derivative 45 $0.00 $0.00
Disclosure

SEC source: 0001371285-26-000054 · wk-form4_1772240561.xml · derivative · entry 12

GALLAGHER JOHN R · CIK 0001967117 · Chief Operating Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 270

Underlying: Common Stock · 45 shares

Expires 2027-08-25

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · derivative.exercise_price: Restricted stock units convert into common stock on a one-for-one basis.

F7 · derivative.exercise_date: On August 14, 2023, the reporting person was granted 721 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.

F7 · derivative.expiration_date: On August 14, 2023, the reporting person was granted 721 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.

Read SEC document
February 25, 2026 Filed Feb 28, 2026 01:02 UTC TRUPANION, INC. TRUP · Entity 4822 Exercise / conversionRestricted Stock Unit (RSU) · Derivative 451 $0.00 $0.00
Disclosure

SEC source: 0001371285-26-000054 · wk-form4_1772240561.xml · derivative · entry 11

GALLAGHER JOHN R · CIK 0001967117 · Chief Operating Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 2,709

Underlying: Common Stock · 451 shares

Expires 2027-08-25

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · derivative.exercise_price: Restricted stock units convert into common stock on a one-for-one basis.

F6 · derivative.exercise_date: On August 14, 2023, the reporting person was granted 7,223 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.

F6 · derivative.expiration_date: On August 14, 2023, the reporting person was granted 7,223 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.

Read SEC document
February 25, 2026 Filed Feb 28, 2026 01:02 UTC TRUPANION, INC. TRUP · Entity 4822 Exercise / conversionRestricted Stock Unit (RSU) · Derivative 29 $0.00 $0.00
Disclosure

SEC source: 0001371285-26-000054 · wk-form4_1772240561.xml · derivative · entry 10

GALLAGHER JOHN R · CIK 0001967117 · Chief Operating Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 144

Underlying: Common Stock · 29 shares

Expires 2027-05-25

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F4 · derivative.exercise_price: The RSUs convert into common stock on a one-for-one basis.

F5 · derivative.exercise_date: On May 15, 2023, the reporting person was granted 460 restricted stock units (RSUs). The RSUs vested and converted into common stock of the Issuer as to 1/4th of the total shares on May 25, 2024, after which 1/16th of the total shares vest quarterly, subject to continued service through each vest date.

F5 · derivative.expiration_date: On May 15, 2023, the reporting person was granted 460 restricted stock units (RSUs). The RSUs vested and converted into common stock of the Issuer as to 1/4th of the total shares on May 25, 2024, after which 1/16th of the total shares vest quarterly, subject to continued service through each vest date.

Read SEC document
February 25, 2026 Filed Feb 28, 2026 01:02 UTC TRUPANION, INC. TRUP · Entity 4822 Exercise / conversionRestricted Stock Unit (RSU) · Derivative 735 $0.00 $0.00
Disclosure

SEC source: 0001371285-26-000054 · wk-form4_1772240561.xml · derivative · entry 9

GALLAGHER JOHN R · CIK 0001967117 · Chief Operating Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 0

Underlying: Common Stock · 735 shares

Expires 2026-02-25

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · derivative.exercise_price: Restricted stock units convert into common stock on a one-for-one basis.

F3 · derivative.exercise_date: On February 28, 2022, the reporting person was granted 11,752 restricted stock units (RSUs). The RSUs vested and converted into common stock of the Issuer as to 1/4th of the total shares on February 25, 2023, after which 1/16th of the total shares vest quarterly, subject to continued service through each vest date.

F3 · derivative.expiration_date: On February 28, 2022, the reporting person was granted 11,752 restricted stock units (RSUs). The RSUs vested and converted into common stock of the Issuer as to 1/4th of the total shares on February 25, 2023, after which 1/16th of the total shares vest quarterly, subject to continued service through each vest date.

Read SEC document
February 25, 2026 Filed Feb 28, 2026 01:02 UTC TRUPANION, INC. TRUP · Entity 4822 Tax withholdingCommon Stock 10 $26.70 $267.00
Disclosure

SEC source: 0001371285-26-000054 · wk-form4_1772240561.xml · nonDerivative · entry 8

GALLAGHER JOHN R · CIK 0001967117 · Chief Operating Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 37,670

F2 · shares: 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.

Read SEC document
February 25, 2026 Filed Feb 28, 2026 01:02 UTC TRUPANION, INC. TRUP · Entity 4822 Exercise / conversionCommon Stock 45 Not disclosed Not disclosed
Disclosure

SEC source: 0001371285-26-000054 · wk-form4_1772240561.xml · nonDerivative · entry 7

GALLAGHER JOHN R · CIK 0001967117 · Chief Operating Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 37,680

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · price: Restricted stock units convert into common stock on a one-for-one basis.

Read SEC document

Value uses the disclosed total when available, otherwise shares × reported transaction price. It is not an estimate of exercise cash cost or investment performance.