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WHEELER SIMON

Disclosed activity across 1 company

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19416
SEC CIK
0001966923

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Reported relationships

Latest disclosed role at each company.

CompanyLast reported asReport datePublished
TRUPANION, INC.TRUP · Entity 4822EVP, Trupanion InternationalAugust 22, 2026August 26, 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 August 22, 2026 · Filed August 26, 2026

Security / awardOwnership accountDisclosed shares / unitsDisclosure context
Common StockSEC Table I · non-derivativeDirect25,327 Ending reported balance After 2026-08-25 transaction · row 8
8 source rows · reconciled sequence

Row 1 · 2026-08-22 · Exercise / conversion · Acquired 528 · Balance 24,767

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

Row 2 · 2026-08-22 · Tax withholding · Disposed 263 · Balance 24,504

F2: 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.

Row 3 · 2026-08-22 · Exercise / conversion · Acquired 385 · Balance 24,889

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

Row 4 · 2026-08-22 · Tax withholding · Disposed 192 · Balance 24,697

F2: 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.

Row 5 · 2026-08-22 · Exercise / conversion · Acquired 938 · Balance 25,635

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

Row 6 · 2026-08-22 · Tax withholding · Disposed 469 · Balance 25,166

F2: 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.

Row 7 · 2026-08-25 · Exercise / conversion · Acquired 322 · Balance 25,488

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

Row 8 · 2026-08-25 · Tax withholding · Disposed 161 · Balance 25,327

F2: 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.

Restricted Stock Unit (RSU)SEC Table II · derivative / convertible security · Expires 2027-02-22Direct1,055 Reported balance After 2026-08-22 transaction · row 9 Instrument identity requires review; Table II rows are not merged.
1 source row

Row 9 · 2026-08-22 · Exercise / conversion · Disposed 528 · Balance 1,055

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

F3: On February 27, 2025, the reporting person was granted 4,219 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.

Restricted Stock Unit (RSU)SEC Table II · derivative / convertible security · Expires 2028-02-22Direct2,310 Reported balance After 2026-08-22 transaction · row 10 Instrument identity requires review; Table II rows are not merged.
1 source row

Row 10 · 2026-08-22 · Exercise / conversion · Disposed 385 · Balance 2,310

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

F4: On February 20, 2026, the reporting person was granted 3,079 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.

Restricted Stock Unit (RSU)SEC Table II · derivative / convertible security · Expires 2028-02-25Direct5,625 Reported balance After 2026-08-22 transaction · row 11 Instrument identity requires review; Table II rows are not merged.
1 source row

Row 11 · 2026-08-22 · Exercise / conversion · Disposed 938 · Balance 5,625

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

F5: On February 27, 2024, the reporting person was granted 15,000 restricted stock units (RSUs). The RSUs vest and convert into common stock of the Issuer as to 1/4th of the total shares on February 25, 2025, after which 1/16th of the total shares vest quarterly, subject to continued service through each vest date.

Restricted Stock Unit (RSU)SEC Table II · derivative / convertible security · Expires 2027-08-25Direct1,286 Reported balance After 2026-08-25 transaction · row 12 Instrument identity requires review; Table II rows are not merged.
1 source row

Row 12 · 2026-08-25 · Exercise / conversion · Disposed 322 · Balance 1,286

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

F6: On August 14, 2023, the reporting person was granted 5,144 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.

Filing footnotes · ownership attribution and instrument terms

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

F2: 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.

F3: On February 27, 2025, the reporting person was granted 4,219 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: On February 20, 2026, the reporting person was granted 3,079 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: On February 27, 2024, the reporting person was granted 15,000 restricted stock units (RSUs). The RSUs vest and convert into common stock of the Issuer as to 1/4th of the total shares on February 25, 2025, after which 1/16th of the total shares vest quarterly, subject to continued service through each vest date.

F6: On August 14, 2023, the reporting person was granted 5,144 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.

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
August 25, 2026 Filed Aug 26, 2026 22:56 UTC TRUPANION, INC. TRUP · Entity 4822 Exercise / conversionRestricted Stock Unit (RSU) · Derivative 322 $0.00 $0.00
Disclosure

SEC source: 0001371285-26-000192 · wk-form4_1787784997.xml · derivative · entry 12

WHEELER SIMON · CIK 0001966923 · EVP, Trupanion International

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 1,286

Underlying: Common Stock · 322 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 5,144 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 5,144 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 Tax withholdingCommon Stock 161 $31.84 $5,126.24
Disclosure

SEC source: 0001371285-26-000192 · wk-form4_1787784997.xml · nonDerivative · entry 8

WHEELER SIMON · CIK 0001966923 · EVP, Trupanion International

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 25,327

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 322 Not disclosed Not disclosed
Disclosure

SEC source: 0001371285-26-000192 · wk-form4_1787784997.xml · nonDerivative · entry 7

WHEELER SIMON · CIK 0001966923 · EVP, Trupanion International

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 25,488

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 938 $0.00 $0.00
Disclosure

SEC source: 0001371285-26-000192 · wk-form4_1787784997.xml · derivative · entry 11

WHEELER SIMON · CIK 0001966923 · EVP, Trupanion International

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 5,625

Underlying: Common Stock · 938 shares

Expires 2028-02-25

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.

F5 · derivative.exercise_date: On February 27, 2024, the reporting person was granted 15,000 restricted stock units (RSUs). The RSUs vest and convert into common stock of the Issuer as to 1/4th of the total shares on February 25, 2025, after which 1/16th of the total shares vest quarterly, subject to continued service through each vest date.

F5 · derivative.expiration_date: On February 27, 2024, the reporting person was granted 15,000 restricted stock units (RSUs). The RSUs vest and convert into common stock of the Issuer as to 1/4th of the total shares on February 25, 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 Exercise / conversionRestricted Stock Unit (RSU) · Derivative 385 $0.00 $0.00
Disclosure

SEC source: 0001371285-26-000192 · wk-form4_1787784997.xml · derivative · entry 10

WHEELER SIMON · CIK 0001966923 · EVP, Trupanion International

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 2,310

Underlying: Common Stock · 385 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.

F4 · derivative.exercise_date: On February 20, 2026, the reporting person was granted 3,079 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.

F4 · derivative.expiration_date: On February 20, 2026, the reporting person was granted 3,079 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 528 $0.00 $0.00
Disclosure

SEC source: 0001371285-26-000192 · wk-form4_1787784997.xml · derivative · entry 9

WHEELER SIMON · CIK 0001966923 · EVP, Trupanion International

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 1,055

Underlying: Common Stock · 528 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.

F3 · derivative.exercise_date: On February 27, 2025, the reporting person was granted 4,219 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.

F3 · derivative.expiration_date: On February 27, 2025, the reporting person was granted 4,219 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 Tax withholdingCommon Stock 469 $31.76 $14,895.44
Disclosure

SEC source: 0001371285-26-000192 · wk-form4_1787784997.xml · nonDerivative · entry 6

WHEELER SIMON · CIK 0001966923 · EVP, Trupanion International

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 25,166

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 938 Not disclosed Not disclosed
Disclosure

SEC source: 0001371285-26-000192 · wk-form4_1787784997.xml · nonDerivative · entry 5

WHEELER SIMON · CIK 0001966923 · EVP, Trupanion International

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 25,635

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 192 $31.76 $6,097.92
Disclosure

SEC source: 0001371285-26-000192 · wk-form4_1787784997.xml · nonDerivative · entry 4

WHEELER SIMON · CIK 0001966923 · EVP, Trupanion International

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 24,697

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 385 Not disclosed Not disclosed
Disclosure

SEC source: 0001371285-26-000192 · wk-form4_1787784997.xml · nonDerivative · entry 3

WHEELER SIMON · CIK 0001966923 · EVP, Trupanion International

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 24,889

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 263 $31.76 $8,352.88
Disclosure

SEC source: 0001371285-26-000192 · wk-form4_1787784997.xml · nonDerivative · entry 2

WHEELER SIMON · CIK 0001966923 · EVP, Trupanion International

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 24,504

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 528 Not disclosed Not disclosed
Disclosure

SEC source: 0001371285-26-000192 · wk-form4_1787784997.xml · nonDerivative · entry 1

WHEELER SIMON · CIK 0001966923 · EVP, Trupanion International

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 24,767

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 01:57 UTC TRUPANION, INC. TRUP · Entity 4822 Exercise / conversionRestricted Stock Unit (RSU) · Derivative 321 $0.00 $0.00
Disclosure

SEC source: 0001371285-26-000144 · wk-form4_1779933423.xml · derivative · entry 12

WHEELER SIMON · CIK 0001966923 · EVP, Trupanion International

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 1,608

Underlying: Common Stock · 321 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 5,144 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 5,144 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 01:57 UTC TRUPANION, INC. TRUP · Entity 4822 Tax withholdingCommon Stock 150 $21.86 $3,279.00
Disclosure

SEC source: 0001371285-26-000144 · wk-form4_1779933423.xml · nonDerivative · entry 8

WHEELER SIMON · CIK 0001966923 · EVP, Trupanion International

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 24,239

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 01:57 UTC TRUPANION, INC. TRUP · Entity 4822 Exercise / conversionCommon Stock 321 Not disclosed Not disclosed
Disclosure

SEC source: 0001371285-26-000144 · wk-form4_1779933423.xml · nonDerivative · entry 7

WHEELER SIMON · CIK 0001966923 · EVP, Trupanion International

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 24,389

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 01:57 UTC TRUPANION, INC. TRUP · Entity 4822 Exercise / conversionRestricted Stock Unit (RSU) · Derivative 937 $0.00 $0.00
Disclosure

SEC source: 0001371285-26-000144 · wk-form4_1779933423.xml · derivative · entry 11

WHEELER SIMON · CIK 0001966923 · EVP, Trupanion International

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 7,501

Underlying: Common Stock · 937 shares

Expires 2028-02-25

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.

F5 · derivative.exercise_date: On February 27, 2024, the reporting person was granted 15,000 restricted stock units (RSUs). The RSUs vest and convert into common stock of the Issuer as to 1/4th of the total shares on February 25, 2025, after which 1/16th of the total shares vest quarterly, subject to continued service through each vest date.

F5 · derivative.expiration_date: On February 27, 2024, the reporting person was granted 15,000 restricted stock units (RSUs). The RSUs vest and convert into common stock of the Issuer as to 1/4th of the total shares on February 25, 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 01:57 UTC TRUPANION, INC. TRUP · Entity 4822 Exercise / conversionRestricted Stock Unit (RSU) · Derivative 384 $0.00 $0.00
Disclosure

SEC source: 0001371285-26-000144 · wk-form4_1779933423.xml · derivative · entry 10

WHEELER SIMON · CIK 0001966923 · EVP, Trupanion International

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 2,695

Underlying: Common Stock · 384 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.

F4 · derivative.exercise_date: On February 20, 2026, the reporting person was granted 3,079 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.

F4 · derivative.expiration_date: On February 20, 2026, the reporting person was granted 3,079 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
May 22, 2026 Filed May 28, 2026 01:57 UTC TRUPANION, INC. TRUP · Entity 4822 Exercise / conversionRestricted Stock Unit (RSU) · Derivative 527 $0.00 $0.00
Disclosure

SEC source: 0001371285-26-000144 · wk-form4_1779933423.xml · derivative · entry 9

WHEELER SIMON · CIK 0001966923 · EVP, Trupanion International

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 1,583

Underlying: Common Stock · 527 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.

F3 · derivative.exercise_date: On February 27, 2025, the reporting person was granted 4,219 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.

F3 · derivative.expiration_date: On February 27, 2025, the reporting person was granted 4,219 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 01:57 UTC TRUPANION, INC. TRUP · Entity 4822 Tax withholdingCommon Stock 180 $21.98 $3,956.40
Disclosure

SEC source: 0001371285-26-000144 · wk-form4_1779933423.xml · nonDerivative · entry 6

WHEELER SIMON · CIK 0001966923 · EVP, Trupanion International

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 24,068

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 01:57 UTC TRUPANION, INC. TRUP · Entity 4822 Exercise / conversionCommon Stock 384 Not disclosed Not disclosed
Disclosure

SEC source: 0001371285-26-000144 · wk-form4_1779933423.xml · nonDerivative · entry 5

WHEELER SIMON · CIK 0001966923 · EVP, Trupanion International

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 24,248

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 01:57 UTC TRUPANION, INC. TRUP · Entity 4822 Tax withholdingCommon Stock 247 $21.98 $5,429.06
Disclosure

SEC source: 0001371285-26-000144 · wk-form4_1779933423.xml · nonDerivative · entry 4

WHEELER SIMON · CIK 0001966923 · EVP, Trupanion International

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 23,864

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 01:57 UTC TRUPANION, INC. TRUP · Entity 4822 Exercise / conversionCommon Stock 527 Not disclosed Not disclosed
Disclosure

SEC source: 0001371285-26-000144 · wk-form4_1779933423.xml · nonDerivative · entry 3

WHEELER SIMON · CIK 0001966923 · EVP, Trupanion International

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 24,111

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 01:57 UTC TRUPANION, INC. TRUP · Entity 4822 Tax withholdingCommon Stock 440 $21.98 $9,671.20
Disclosure

SEC source: 0001371285-26-000144 · wk-form4_1779933423.xml · nonDerivative · entry 2

WHEELER SIMON · CIK 0001966923 · EVP, Trupanion International

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 23,584

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 01:57 UTC TRUPANION, INC. TRUP · Entity 4822 Exercise / conversionCommon Stock 937 Not disclosed Not disclosed
Disclosure

SEC source: 0001371285-26-000144 · wk-form4_1779933423.xml · nonDerivative · entry 1

WHEELER SIMON · CIK 0001966923 · EVP, Trupanion International

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 24,024

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 Jun 2, 2026 00:37 UTC Amendment TRUPANION, INC. TRUP · Entity 4822 Exercise / conversionRestricted Stock Unit (RSU) · Derivative 937 $0.00 $0.00
Disclosure

SEC source: 0001371285-26-000149 · wk-form4a_1780360636.xml · derivative · entry 1

WHEELER SIMON · CIK 0001966923 · EVP, Trupanion International

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 6,563

Underlying: Common Stock · 937 shares

Expires 2028-02-25

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.

F2 · derivative.exercise_date: On February 27, 2024, the reporting person was granted 15,000 restricted stock units (RSUs). The RSUs vest and convert into common stock of the Issuer as to 1/4th of the total shares on February 25, 2025, after which 1/16th of the total shares vest quarterly, subject to continued service through each vest date.

F2 · derivative.expiration_date: On February 27, 2024, the reporting person was granted 15,000 restricted stock units (RSUs). The RSUs vest and convert into common stock of the Issuer as to 1/4th of the total shares on February 25, 2025, after which 1/16th of the total shares vest quarterly, subject to continued service through each vest date.

F3 · balance_after: This Form 4 is being filed to correct a clerical error in previously reported holdings of derivative securities for RSU dated 2/27/24 for 15,000 shares. In the Form 4 filed on November 25, 2025, the number of derivative securities beneficially owned following the reported transaction was incorrectly reported; the correct amount beneficially owned as of November 25, 2025 was 8,438. In addition, the Form 4 filed on February 24, 2026 incorrectly reported the number of derivative securities beneficially owned following the reported transaction; the correct amount beneficially owned as of February 24, 2026 was 7,500. In addition, the Form 4 filed on May 27, 2026 incorrectly reported the number of derivative securities beneficially owned following the reported transaction; the correct amount beneficially owned as of May 27, 2026 was 6,563.

Read SEC document
February 25, 2026 Filed Feb 28, 2026 01:02 UTC TRUPANION, INC. TRUP · Entity 4822 Exercise / conversionRestricted Stock Unit (RSU) · Derivative 322 $0.00 $0.00
Disclosure

SEC source: 0001371285-26-000056 · wk-form4_1772240573.xml · derivative · entry 3

WHEELER SIMON · CIK 0001966923 · EVP, Trupanion International

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 1,929

Underlying: Common Stock · 322 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.

F3 · derivative.exercise_date: On August 14, 2023, the reporting person was granted 5,144 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.

F3 · derivative.expiration_date: On August 14, 2023, the reporting person was granted 5,144 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 Tax withholdingCommon Stock 151 $26.70 $4,031.70
Disclosure

SEC source: 0001371285-26-000056 · wk-form4_1772240573.xml · nonDerivative · entry 2

WHEELER SIMON · CIK 0001966923 · EVP, Trupanion International

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 23,087

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 322 Not disclosed Not disclosed
Disclosure

SEC source: 0001371285-26-000056 · wk-form4_1772240573.xml · nonDerivative · entry 1

WHEELER SIMON · CIK 0001966923 · EVP, Trupanion International

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 23,238

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
February 22, 2026 Filed Feb 25, 2026 02:11 UTC TRUPANION, INC. TRUP · Entity 4822 Exercise / conversionRestricted Stock Unit (RSU) · Derivative 527 $0.00 $0.00
Disclosure

SEC source: 0001371285-26-000036 · wk-form4_1771985502.xml · derivative · entry 10

WHEELER SIMON · CIK 0001966923 · EVP, Trupanion International

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 2,110

Underlying: Common Stock · 527 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.

F6 · derivative.exercise_date: On February 27, 2025, the reporting person was granted 4,219 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.

F6 · derivative.expiration_date: On February 27, 2025, the reporting person was granted 4,219 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
February 22, 2026 Filed Feb 25, 2026 02:11 UTC TRUPANION, INC. TRUP · Entity 4822 Exercise / conversionRestricted Stock Unit (RSU) · Derivative 1,526 $0.00 $0.00
Disclosure

SEC source: 0001371285-26-000036 · wk-form4_1771985502.xml · derivative · entry 9

WHEELER SIMON · CIK 0001966923 · EVP, Trupanion International

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 6,324

Underlying: Common Stock · 1,526 shares

Expires 2028-02-25

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.

F5 · derivative.exercise_date: On February 27, 2024, the reporting person was granted 15,000 restricted stock units (RSUs). The RSUs vest and convert into common stock of the Issuer as to 1/4th of the total shares on February 25, 2025, after which 1/16th of the total shares vest quarterly, subject to continued service through each vest date.

F5 · derivative.expiration_date: On February 27, 2024, the reporting person was granted 15,000 restricted stock units (RSUs). The RSUs vest and convert into common stock of the Issuer as to 1/4th of the total shares on February 25, 2025, after which 1/16th of the total shares vest quarterly, subject to continued service through each vest date.

Read SEC document
February 22, 2026 Filed Feb 25, 2026 02:11 UTC TRUPANION, INC. TRUP · Entity 4822 Exercise / conversionRestricted Stock Unit (RSU) · Derivative 938 $0.00 $0.00
Disclosure

SEC source: 0001371285-26-000036 · wk-form4_1771985502.xml · derivative · entry 8

WHEELER SIMON · CIK 0001966923 · EVP, Trupanion International

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 1,176

Underlying: Common Stock · 938 shares

Expires 2026-02-22

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, 2024, the reporting person was granted 12,203 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, 2024, 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, 2024, the reporting person was granted 12,203 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, 2024, after which 1/8th of the total shares vest quarterly, subject to continued service through each vest date.

Read SEC document
February 22, 2026 Filed Feb 25, 2026 02:11 UTC TRUPANION, INC. TRUP · Entity 4822 Tax withholdingCommon Stock 247 $27.16 $6,708.52
Disclosure

SEC source: 0001371285-26-000036 · wk-form4_1771985502.xml · nonDerivative · entry 6

WHEELER SIMON · CIK 0001966923 · EVP, Trupanion International

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 22,916

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 22, 2026 Filed Feb 25, 2026 02:11 UTC TRUPANION, INC. TRUP · Entity 4822 Exercise / conversionCommon Stock 527 Not disclosed Not disclosed
Disclosure

SEC source: 0001371285-26-000036 · wk-form4_1771985502.xml · nonDerivative · entry 5

WHEELER SIMON · CIK 0001966923 · EVP, Trupanion International

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 23,163

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
February 22, 2026 Filed Feb 25, 2026 02:11 UTC TRUPANION, INC. TRUP · Entity 4822 Tax withholdingCommon Stock 717 $27.16 $19,473.72
Disclosure

SEC source: 0001371285-26-000036 · wk-form4_1771985502.xml · nonDerivative · entry 4

WHEELER SIMON · CIK 0001966923 · EVP, Trupanion International

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 22,636

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 22, 2026 Filed Feb 25, 2026 02:11 UTC TRUPANION, INC. TRUP · Entity 4822 Exercise / conversionCommon Stock 1,526 Not disclosed Not disclosed
Disclosure

SEC source: 0001371285-26-000036 · wk-form4_1771985502.xml · nonDerivative · entry 3

WHEELER SIMON · CIK 0001966923 · EVP, Trupanion International

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 23,353

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
February 22, 2026 Filed Feb 25, 2026 02:11 UTC TRUPANION, INC. TRUP · Entity 4822 Tax withholdingCommon Stock 440 $27.16 $11,950.40
Disclosure

SEC source: 0001371285-26-000036 · wk-form4_1771985502.xml · nonDerivative · entry 2

WHEELER SIMON · CIK 0001966923 · EVP, Trupanion International

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 21,827

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 22, 2026 Filed Feb 25, 2026 02:11 UTC TRUPANION, INC. TRUP · Entity 4822 Exercise / conversionCommon Stock 938 Not disclosed Not disclosed
Disclosure

SEC source: 0001371285-26-000036 · wk-form4_1771985502.xml · nonDerivative · entry 1

WHEELER SIMON · CIK 0001966923 · EVP, Trupanion International

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 22,267

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
February 22, 2026 Filed Jun 2, 2026 00:37 UTC Amendment TRUPANION, INC. TRUP · Entity 4822 Exercise / conversionRestricted Stock Unit (RSU) · Derivative 1,526 $0.00 $0.00
Disclosure

SEC source: 0001371285-26-000150 · wk-form4a_1780360641.xml · derivative · entry 1

WHEELER SIMON · CIK 0001966923 · EVP, Trupanion International

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 0

Underlying: Common Stock · 1,526 shares

Expires 2026-02-22

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.

F2 · derivative.exercise_date: On February 27, 2024, the reporting person was granted 12,203 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, 2024, after which 1/8th of the total shares vest quarterly, subject to continued service through each vest date.

F2 · derivative.expiration_date: On February 27, 2024, the reporting person was granted 12,203 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, 2024, after which 1/8th of the total shares vest quarterly, subject to continued service through each vest date.

F3 · balance_after: This Form 4 is being filed to correct a clerical error in previously reported holdings of derivative securities for RSU dated 2/27/24 for 12,203 shares. In the Form 4 filed on November 25, 2025, the number of derivative securities beneficially owned following the reported transaction was incorrectly reported; the correct amount beneficially owned as of November 25, 2025 was 1,526. In addition, the Form 4 filed on February 24, 2026 incorrectly reported the number of derivative securities beneficially owned following the reported transaction; the correct amount beneficially owned as of February 24, 2026 was 0.

Read SEC document
February 20, 2026 Filed Feb 25, 2026 02:11 UTC TRUPANION, INC. TRUP · Entity 4822 GrantRestricted Stock Unit (RSU) · Derivative 3,079 $0.00 $0.00
Disclosure

SEC source: 0001371285-26-000036 · wk-form4_1771985502.xml · derivative · entry 7

WHEELER SIMON · CIK 0001966923 · EVP, Trupanion International

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 3,079

Underlying: Common Stock · 3,079 shares

Expires 2028-02-22

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

F3 · derivative.exercise_date: On February 20, 2026, the reporting person was granted 3,079 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.

F3 · derivative.expiration_date: On February 20, 2026, the reporting person was granted 3,079 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
November 25, 2025 Filed Nov 26, 2025 23:27 UTC TRUPANION, INC. TRUP · Entity 4822 Exercise / conversionRestricted Stock Unit (RSU) · Derivative 321 $0.00 $0.00
Disclosure

SEC source: 0001966923-25-000006 · wk-form4_1764199648.xml · derivative · entry 6

WHEELER SIMON · CIK 0001966923 · EVP, Trupanion International

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 2,251

Underlying: Common Stock · 321 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.

F4 · derivative.exercise_date: On August 14, 2023, the reporting person was granted 5,144 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.

F4 · derivative.expiration_date: On August 14, 2023, the reporting person was granted 5,144 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
November 25, 2025 Filed Nov 26, 2025 23:27 UTC TRUPANION, INC. TRUP · Entity 4822 Exercise / conversionRestricted Stock Unit (RSU) · Derivative 975 $0.00 $0.00
Disclosure

SEC source: 0001966923-25-000006 · wk-form4_1764199648.xml · derivative · entry 5

WHEELER SIMON · CIK 0001966923 · EVP, Trupanion International

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 0

Underlying: Common Stock · 975 shares

Expires 2025-11-25

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 November 12, 2021, the reporting person was granted 15,588 restricted stock units (RSUs). The RSUs vested and converted into common stock of the Issuer as to 1/4th of the total shares on November 25, 2022, 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, 2021, the reporting person was granted 15,588 restricted stock units (RSUs). The RSUs vested and converted into common stock of the Issuer as to 1/4th of the total shares on November 25, 2022, after which 1/16th of the total shares vest quarterly, subject to continued service through each vest date.

Read SEC document
November 25, 2025 Filed Nov 26, 2025 23:27 UTC TRUPANION, INC. TRUP · Entity 4822 Tax withholdingCommon Stock 150 $35.36 $5,304.00
Disclosure

SEC source: 0001966923-25-000006 · wk-form4_1764199648.xml · nonDerivative · entry 4

WHEELER SIMON · CIK 0001966923 · EVP, Trupanion International

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 21,329

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
November 25, 2025 Filed Nov 26, 2025 23:27 UTC TRUPANION, INC. TRUP · Entity 4822 Exercise / conversionCommon Stock 321 Not disclosed Not disclosed
Disclosure

SEC source: 0001966923-25-000006 · wk-form4_1764199648.xml · nonDerivative · entry 3

WHEELER SIMON · CIK 0001966923 · EVP, Trupanion International

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 21,479

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
November 25, 2025 Filed Nov 26, 2025 23:27 UTC TRUPANION, INC. TRUP · Entity 4822 Tax withholdingCommon Stock 458 $35.36 $16,194.88
Disclosure

SEC source: 0001966923-25-000006 · wk-form4_1764199648.xml · nonDerivative · entry 2

WHEELER SIMON · CIK 0001966923 · EVP, Trupanion International

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 21,158

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
November 25, 2025 Filed Nov 26, 2025 23:27 UTC TRUPANION, INC. TRUP · Entity 4822 Exercise / conversionCommon Stock 975 Not disclosed Not disclosed
Disclosure

SEC source: 0001966923-25-000006 · wk-form4_1764199648.xml · nonDerivative · entry 1

WHEELER SIMON · CIK 0001966923 · EVP, Trupanion International

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 21,616

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
November 24, 2025 Filed Nov 26, 2025 02:30 UTC TRUPANION, INC. TRUP · Entity 4822 Exercise / conversionRestricted Stock Unit (RSU) · Derivative 1,525 $0.00 $0.00
Disclosure

SEC source: 0001966923-25-000004 · wk-form4_1764124250.xml · derivative · entry 9

WHEELER SIMON · CIK 0001966923 · EVP, Trupanion International

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 7,850

Underlying: Common Stock · 1,525 shares

Expires 2028-02-25

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.

F5 · derivative.exercise_date: On February 27, 2024, the reporting person was granted 15,000 restricted stock units (RSUs). The RSUs vest and convert into common stock of the Issuer as to 1/4th of the total shares on February 25, 2025, after which 1/16th of the total shares vest quarterly, subject to continued service through each vest date.

F5 · derivative.expiration_date: On February 27, 2024, the reporting person was granted 15,000 restricted stock units (RSUs). The RSUs vest and convert into common stock of the Issuer as to 1/4th of the total shares on February 25, 2025, after which 1/16th of the total shares vest quarterly, subject to continued service through each vest date.

Read SEC document
November 24, 2025 Filed Nov 26, 2025 02:30 UTC TRUPANION, INC. TRUP · Entity 4822 Exercise / conversionRestricted Stock Unit (RSU) · Derivative 937 $0.00 $0.00
Disclosure

SEC source: 0001966923-25-000004 · wk-form4_1764124250.xml · derivative · entry 8

WHEELER SIMON · CIK 0001966923 · EVP, Trupanion International

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 2,114

Underlying: Common Stock · 937 shares

Expires 2026-02-22

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, 2024, the reporting person was granted 12,203 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, 2024, 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, 2024, the reporting person was granted 12,203 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, 2024, after which 1/8th of the total shares vest quarterly, subject to continued service through each vest date.

Read SEC document
November 24, 2025 Filed Nov 26, 2025 02:30 UTC TRUPANION, INC. TRUP · Entity 4822 Exercise / conversionRestricted Stock Unit (RSU) · Derivative 528 $0.00 $0.00
Disclosure

SEC source: 0001966923-25-000004 · wk-form4_1764124250.xml · derivative · entry 7

WHEELER SIMON · CIK 0001966923 · EVP, Trupanion International

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 2,637

Underlying: Common Stock · 528 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.

F3 · derivative.exercise_date: On February 27, 2025, the reporting person was granted 4,219 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.

F3 · derivative.expiration_date: On February 27, 2025, the reporting person was granted 4,219 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
November 24, 2025 Filed Nov 26, 2025 02:30 UTC TRUPANION, INC. TRUP · Entity 4822 Tax withholdingCommon Stock 716 $35.40 $25,346.40
Disclosure

SEC source: 0001966923-25-000004 · wk-form4_1764124250.xml · nonDerivative · entry 6

WHEELER SIMON · CIK 0001966923 · EVP, Trupanion International

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 20,641

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.

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November 24, 2025 Filed Nov 26, 2025 02:30 UTC TRUPANION, INC. TRUP · Entity 4822 Exercise / conversionCommon Stock 1,525 Not disclosed Not disclosed
Disclosure

SEC source: 0001966923-25-000004 · wk-form4_1764124250.xml · nonDerivative · entry 5

WHEELER SIMON · CIK 0001966923 · EVP, Trupanion International

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 21,357

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.

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