Gavin Friedman - May 25, 2021 Form 4 Insider Report for TRUPANION, INC. (TRUP)

Role: EVP, People and Legal
Signature: /s/ Charlotte Sim-Warner as attorney-in-fact for Gavin Friedman
Stock symbol: TRUP
Transactions as of: May 25, 2021
Transactions value $: -$123,447
Form type: 4
Date filed: 5/27/2021, 06:46 PM
Next filing: Jun 3, 2021

Transactions Table

Type	Sym	Class	Transaction	Value $	Shares	Change %	* Price $	Shares After	Date	Ownership	Footnotes
transaction	TRUP	Common Stock	Options Exercise		+312	+57.67%		853	May 25, 2021	Direct	F1
transaction	TRUP	Common Stock	Tax liability	-$10.2K	-122	-14.3%	$83.41	731	May 25, 2021	Direct	F2
transaction	TRUP	Common Stock	Options Exercise		+684	+93.57%		1.42K	May 25, 2021	Direct	F1
transaction	TRUP	Common Stock	Tax liability	-$22.4K	-269	-19.01%	$83.41	1.15K	May 25, 2021	Direct	F2
transaction	TRUP	Common Stock	Options Exercise		+23	+2.01%		1.17K	May 25, 2021	Direct	F1
transaction	TRUP	Common Stock	Tax liability	-$751	-9	-0.77%	$83.41	1.16K	May 25, 2021	Direct	F2
transaction	TRUP	Common Stock	Options Exercise		+2.75K	+236.72%		3.91K	May 25, 2021	Direct	F1
transaction	TRUP	Common Stock	Tax liability	-$90.1K	-1.08K	-27.65%	$83.41	2.83K	May 25, 2021	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	-312	-24.96%	$0.00	938	May 25, 2021	Common Stock	312		Direct	F1, F3
transaction	TRUP	Restricted Stock Unit (RSU)	Options Exercise	$0	-684	-12.5%	$0.00	4.79K	May 25, 2021	Common Stock	684		Direct	F1, F4
transaction	TRUP	Restricted Stock Unit (RSU)	Options Exercise	$0	-23	-9.16%	$0.00	228	May 25, 2021	Common Stock	23		Direct	F1, F5
transaction	TRUP	Restricted Stock Unit (RSU)	Options Exercise	$0	-2.75K	-8.33%	$0.00	30.2K	May 25, 2021	Common Stock	2.75K		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	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.
F4	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.
F5	The RSU vests and will convert to common stock of the Issuer as to 1/4th of the total shares on November 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.