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

Role: President
Signature: /s/ Charlotte Sim-Warner as attorney-in-fact for Margaret Tooth
Stock symbol: TRUP
Transactions as of: Feb 25, 2023
Transactions value $: -$312,441
Form type: 4
Date filed: 2/28/2023, 03:43 PM
Previous filing: Nov 29, 2022
Next filing: May 30, 2023

Transactions Table

Type	Sym	Class	Transaction	Value $	Shares	Change %	* Price $	Shares After	Date	Ownership	Footnotes
transaction	TRUP	Common Stock	Options Exercise		+2.38K	+5.72%		44K	Feb 25, 2023	Direct	F1
transaction	TRUP	Common Stock	Tax liability	-$38.6K	-682	-1.55%	$56.53	43.3K	Feb 25, 2023	Direct	F2
transaction	TRUP	Common Stock	Options Exercise		+2.17K	+5.02%		45.4K	Feb 25, 2023	Direct	F1
transaction	TRUP	Common Stock	Tax liability	-$29.7K	-525	-1.16%	$56.53	44.9K	Feb 25, 2023	Direct	F2
transaction	TRUP	Common Stock	Options Exercise		+2.93K	+6.52%		47.8K	Feb 25, 2023	Direct	F1
transaction	TRUP	Common Stock	Tax liability	-$40.2K	-712	-1.49%	$56.53	47.1K	Feb 25, 2023	Direct	F2
transaction	TRUP	Common Stock	Options Exercise	$0	+13.1K	+27.71%	$0.00	60.2K	Feb 25, 2023	Direct
transaction	TRUP	Common Stock	Tax liability	-$204K	-3.61K	-5.99%	$56.53	56.6K	Feb 25, 2023	Direct	F2

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	-2.38K	-100%	$0.00^*	0	Feb 25, 2023	Common Stock	2.38K		Direct	F1, F3
transaction	TRUP	Restricted Stock Unit (RSU)	Options Exercise	$0	-2.17K	-20.01%	$0.00	8.69K	Feb 25, 2023	Common Stock	2.17K		Direct	F1, F4
transaction	TRUP	Restricted Stock Unit (RSU)	Options Exercise	$0	-2.93K	-11.11%	$0.00	23.4K	Feb 25, 2023	Common Stock	2.93K		Direct	F1, F5
transaction	TRUP	Restricted Stock Unit (RSU)	Award	$0	-13.1K	-25%	$0.00	39.2K	Feb 25, 2023	Common Stock	13.1K		Direct	F1, F6

* 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	On February 22, 2019, the Reporting Person was granted 38,020 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, 2020, after which 1/16th of the total shares vest quarterly, subject to continued service through each vesting date.
F4	On April 3, 2020, the Reporting Person was granted 34,741 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.
F5	On February 22, 2021, the Reporting Person was granted 46,828 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.
F6	On February 28, 2022, the Reporting Person was granted 52,250 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.