Gavin Friedman - 25 May 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
Issuer symbol: TRUP
Transactions as of: 25 May 2021
Net transactions value: -$123,447
Form type: 4
Filing time: 27 May 2021, 18:46:56 UTC
Next filing: 03 Jun 2021
SEC: View on sec.gov

Transactions Table

Type	Sym	Class	Transaction	Value $	Shares	Change %	* Price $	Shares After	Date	Ownership	Footnotes
transaction	TRUP	Common Stock	Options Exercise		+312	+58%		853	25 May 2021	Direct	F1
transaction	TRUP	Common Stock	Tax liability	$10,176	-122	-14%	$83.41	731	25 May 2021	Direct	F2
transaction	TRUP	Common Stock	Options Exercise		+684	+94%		1,415	25 May 2021	Direct	F1
transaction	TRUP	Common Stock	Tax liability	$22,437	-269	-19%	$83.41	1,146	25 May 2021	Direct	F2
transaction	TRUP	Common Stock	Options Exercise		+23	+2%		1,169	25 May 2021	Direct	F1
transaction	TRUP	Common Stock	Tax liability	$751	-9	-0.77%	$83.41	1,160	25 May 2021	Direct	F2
transaction	TRUP	Common Stock	Options Exercise		+2,746	+237%		3,906	25 May 2021	Direct	F1
transaction	TRUP	Common Stock	Tax liability	$90,083	-1,080	-28%	$83.41	2,826	25 May 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	-25%	$0.000000	938	25 May 2021	Common Stock	312		Direct	F1, F3
transaction	TRUP	Restricted Stock Unit (RSU)	Options Exercise	$0	-684	-12%	$0.000000	4,788	25 May 2021	Common Stock	684		Direct	F1, F4
transaction	TRUP	Restricted Stock Unit (RSU)	Options Exercise	$0	-23	-9.2%	$0.000000	228	25 May 2021	Common Stock	23		Direct	F1, F5
transaction	TRUP	Restricted Stock Unit (RSU)	Options Exercise	$0	-2,746	-8.3%	$0.000000	30,210	25 May 2021	Common Stock	2,746		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.