TRUPANION, INC. — Director's Dealing 2021

Feb 27, 2021

SEC Form 4 — Statement of Changes in Beneficial Ownership

Issuer: TRUPANION, INC. (TRUP)
CIK: 0001371285
Period of Report: 2021-02-24

Reporting Person: RAWLINGS DARRYL (Director, CEO)

Non-Derivative Transactions

Date	Security	Code	Shares	Price	A/D	Holdings After	Ownership
2021-02-24	Common Stock	M	70507	$1.04	Acquired	453146	Direct
2021-02-24	Common Stock	S	70507	$102.282	Disposed	382639	Direct
2021-02-24	Common Stock	M	24189	$1.04	Acquired	406828	Direct
2021-02-24	Common Stock	S	24189	$96.251	Disposed	382639	Direct
2021-02-24	Common Stock	M	214362	$1.04	Acquired	597001	Direct
2021-02-24	Common Stock	S	2240	$97.648	Disposed	594761	Direct
2021-02-24	Common Stock	M	621	$1.04	Acquired	595382	Direct
2021-02-24	Common Stock	S	182	$97.648	Disposed	595200	Direct

Derivative Transactions

Date	Security	Exercise Price	Code	Shares	A/D	Expiration	Underlying	Ownership
2021-02-24	Stock Option (right to buy)	$1.04	M	70507	Disposed	2021-09-23	Common Stock (70507.0)	Direct
2021-02-24	Stock Option (right to buy)	$1.04	M	24189	Disposed	2021-09-23	Common Stock (24189.0)	Direct
2021-02-24	Stock Option (right to buy)	$1.04	M	214362	Disposed	2021-09-23	Common Stock (214362.0)	Direct
2021-02-24	Stock Option (right to buy)	$1.04	M	621	Disposed	2021-09-23	Common Stock (621.0)	Direct

Footnotes

F1: The reporting person has exercised all outstanding incentive stock options that are expiring in 2021.

F2: The subsequent sales made are to cover tax obligations associated with the incentive stock option exercises.

F3: The reported price in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $102.00 to $103.995 per share, inclusive. The reporting person undertakes to provide to the issuer, any security holder of the issuer, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the range set forth in this footnote (3).

F4: The reported price in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $94.16 to $100.97 per share, inclusive. The reporting person undertakes to provide to the issuer, any security holder of the issuer, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the range set forth in this footnote (4).

F5: The reported price in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $96.74 to $98.82 per share, inclusive. The reporting person undertakes to provide to the issuer, any security holder of the issuer, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the range set forth in this footnote (5).

F6: The option vested as to 1/4 of the total shares on September 23, 2012, with an additional 1/48th of the total shares vesting monthly thereafter, subject to continued service through each vesting date.