TRUPANION, INC. — Director's Dealing 2021

May 28, 2021

SEC Form 4 — Statement of Changes in Beneficial Ownership

Issuer: TRUPANION, INC. (TRUP)
CIK: 0001371285
Period of Report: 2021-05-25

Reporting Person: RAWLINGS DARRYL (Director, CEO)

Non-Derivative Transactions

Date	Security	Code	Shares	Price	A/D	Holdings After	Ownership
2021-05-25	Common Stock	M	1219	—	Acquired	544162	Direct
2021-05-25	Common Stock	F	479	$83.41	Disposed	543683	Direct
2021-05-25	Common Stock	M	1505	—	Acquired	545188	Direct
2021-05-25	Common Stock	F	592	$83.41	Disposed	544596	Direct
2021-05-25	Common Stock	M	2097	—	Acquired	546693	Direct
2021-05-25	Common Stock	F	825	$83.41	Disposed	545868	Direct
2021-05-26	Common Stock	S	4000	$85.08	Disposed	1003222	Indirect

Derivative Transactions

Date	Security	Exercise Price	Code	Shares	A/D	Expiration	Underlying	Ownership
2021-05-25	Restricted Stock Unit (RSU)	$	M	1219	Disposed	2022-02-25	Common Stock (1219.0)	Direct
2021-05-25	Restricted Stock Unit (RSU)	$	M	1505	Disposed	2023-02-25	Common Stock (1505.0)	Direct
2021-05-25	Restricted Stock Unit (RSU)	$	M	2097	Disposed	2024-02-25	Common Stock (2097.0)	Direct

Footnotes

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: The sales reported were effected pursuant to a Rule 10b5-1 trading plan adopted by Kuyashii Primary Equities LLC. a limited liability company indirectly, wholly-owned by the reporting person and reporting person's spouse, on November 3, 2020, in order to implement a plan of financial diversification. Accordingly, the reporting person had no discretion with regard to the timing of the transaction. In aggregate, the reporting person's plan is Rule 10b5-1 trading plan is part of a diversification strategy on the part of the reporting person to diversify up to 25% of the reporting person's holdings as of the date of the Company's initial public offering in July 2014 from the inception of the Rule 10b5-1 trading plan through 2025.

F4: The RSU vests and will convert to common stock of the Issuer as to 1/4th of the total shares on February 25, 2019, after which 1/16th of the total shares vest quarterly, subject to continued service through each vesting date.

F5: The RSU vests and will convert to common stock of the Issuer as to 1/4th of the total shares on February 25, 2020, after which 1/16th of the total shares vest quarterly, subject to continued service through each vesting date.

F6: The RSU vests and will convert to common stock of the Issuer as to 1/4th of the total shares on February 25, 2021, after which 1/16th of the total shares vest quarterly, subject to continued service through each vesting date.