Darryl Rawlings - Feb 25, 2023 Form 4 Insider Report for TRUPANION, INC. (TRUP)

Role: Chief Executive Officer, Director
Signature: /s/ Charlotte Sim-Warner as attorney-in-fact for Darryl Rawlings
Stock symbol: TRUP
Transactions as of: Feb 25, 2023
Transactions value $: -$377,357
Form type: 4
Date filed: 2/28/2023, 03:42 PM
Previous filing: Feb 15, 2023
Next filing: Mar 20, 2023

Transactions Table

Type	Sym	Class	Transaction	Value $	Shares	Change %	* Price $	Shares After	Date	Ownership	Footnotes
transaction	TRUP	Common Stock	Options Exercise		+1.51K	+0.26%		570K	Feb 25, 2023	Direct	F1
transaction	TRUP	Common Stock	Tax liability	-$25.2K	-446	-0.08%	$56.53	570K	Feb 25, 2023	Direct	F2
transaction	TRUP	Common Stock	Options Exercise		+2.1K	+0.37%		572K	Feb 25, 2023	Direct	F1
transaction	TRUP	Common Stock	Tax liability	-$30K	-531	-0.09%	$56.53	572K	Feb 25, 2023	Direct	F2
transaction	TRUP	Common Stock	Options Exercise		+2.74K	+0.48%		574K	Feb 25, 2023	Direct	F1
transaction	TRUP	Common Stock	Tax liability	-$37.6K	-666	-0.12%	$56.53	574K	Feb 25, 2023	Direct	F2
transaction	TRUP	Common Stock	Options Exercise	$0	+3.78K	+0.66%	$0.00	577K	Feb 25, 2023	Direct
transaction	TRUP	Common Stock	Tax liability	-$52.1K	-921	-0.16%	$56.53	576K	Feb 25, 2023	Direct	F2
transaction	TRUP	Common Stock	Sale	-$232K	-4K	-0.47%	$58.10	845K	Feb 28, 2023	By Kuyashii Primary Equities LLC	F3

Derivative Securities (e.g., puts, calls, warrants, options, convertible securities)

Type	Sym	Class	Transaction	Value $	Shares	Change %	* Price $	Shares After	Date	Underlying Class	Amount	Exercise Price	Ownership	Footnotes
transaction	TRUP	Restricted Stock Unit (RSU)	Options Exercise	$0	-1.51K	-100%	$0.00^*	0	Feb 25, 2023	Common Stock	1.51K		Direct	F1, F4
transaction	TRUP	Restricted Stock Unit (RSU)	Options Exercise	$0	-2.1K	-20%	$0.00	8.39K	Feb 25, 2023	Common Stock	2.1K		Direct	F1, F5
transaction	TRUP	Restricted Stock Unit (RSU)	Options Exercise	$0	-2.74K	-11.11%	$0.00	21.9K	Feb 25, 2023	Common Stock	2.74K		Direct	F1, F6
transaction	TRUP	Restricted Stock Unit (RSU)	Award	$0	-3.78K	-25%	$0.00	11.3K	Feb 25, 2023	Common Stock	3.78K		Direct	F1, F7

* An asterisk sign (*) next to the price indicates that the price is likely invalid.

Explanation of Responses:

Id	Content
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 11, 2022, 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	On February 22, 2019, the Reporting Person was granted 24,080 restricted stock unites (RSUs). The RSUs vest 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.
F5	On April 3, 2020, the Reporting Person was granted 33,566 restricted stock units (RSUs). The RSUs vest 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.
F6	On February 22, 2021, the Reporting Person was granted 43,804 restricted stock units (RSUs). The RSUs vest and will convert to common stock of the Issuer as to 1/4th of the total shares on February 25, 2022, after which 1/16th of the total shares vest quarterly, subject to continued service through each vest date.
F7	On February 28, 2022, the Reporting Person was granted 15,132 restricted stock units (RSUs). The RSUs vest and will convert to 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.