GALLAGHER JOHN R (Chief Operating Officer) exercised options at TRUPANION, INC.

Option exercise — a mechanical event triggered by vesting or expiry. Not a discretionary conviction trade.

M · 6 exercises

GALLAGHER JOHN R

Filed: 5/28/2026ACC: 0001371285-26-000138

InsiderGALLAGHER JOHN RCIK 1967117

→

IssuerTRUPANION, INC.CIK 1371285

Officer· Chief Operating Officer

Since Feb 2026

-1.65K

Net shares

Net seller

$36.3K

Total sold

Open market trades

0B · 0S

Total transactions

6.79K acquired · 8.44K disposed

Non-Derivative Transactions12

Common Stock

Direct

M · Option Exercise

+865.00

Price / share

—

Trade value

—

% of position

2.7%

5/22/2026

31.53K→32.39K

Common Stock

Direct

F · Tax Withholding

−210.00

Price / share

$21.98

Trade value

$4.62K

% of position

0.6%

5/22/2026

32.39K→32.18K

Common Stock

Direct

M · Option Exercise

+3.33K

Price / share

—

Trade value

—

% of position

10.3%

5/22/2026

32.18K→35.51K

Common Stock

Direct

F · Tax Withholding

−810.00

Price / share

$21.98

Trade value

$17.80K

% of position

2.3%

5/22/2026

35.51K→34.70K

Common Stock

Direct

M · Option Exercise

+2.08K

Price / share

—

Trade value

—

% of position

6.0%

5/22/2026

34.70K→36.77K

Common Stock

Direct

F · Tax Withholding

−505.00

Price / share

$21.98

Trade value

$11.10K

% of position

1.4%

5/22/2026

36.77K→36.27K

Common Stock

Direct

M · Option Exercise

+29.00

Price / share

—

Trade value

—

% of position

0.1%

5/25/2026

36.27K→36.30K

Common Stock

Direct

F · Tax Withholding

−7.00

Price / share

$21.86

Trade value

$153.02

% of position

0.0%

5/25/2026

36.30K→36.29K

Common Stock

Direct

M · Option Exercise

+451.00

Price / share

—

Trade value

—

% of position

1.2%

5/25/2026

36.29K→36.74K

Common Stock

Direct

F · Tax Withholding

−109.00

Price / share

$21.86

Trade value

$2.38K

% of position

0.3%

5/25/2026

36.74K→36.63K

Common Stock

Direct

M · Option Exercise

+45.00

Price / share

—

Trade value

—

% of position

0.1%

5/25/2026

36.63K→36.68K

Common Stock

Direct

F · Tax Withholding

−10.00

Price / share

$21.86

Trade value

$218.60

% of position

0.0%

5/25/2026

36.68K→36.67K

Total

Net shares

+5.14K

Net value

-$36.27K

Security	Date	Type	Shares	Price / Share	Trade Value	% of Position	Held Before	Held After
Common Stock Direct	5/22/2026	M · Option Exercise	+865.00	—	—	2.7%	31.53K	32.39K
Common Stock Direct	5/22/2026	F · Tax Withholding	−210.00	$21.98	$4.62K	0.6%	32.39K	32.18K
Common Stock Direct	5/22/2026	M · Option Exercise	+3.33K	—	—	10.3%	32.18K	35.51K
Common Stock Direct	5/22/2026	F · Tax Withholding	−810.00	$21.98	$17.80K	2.3%	35.51K	34.70K
Common Stock Direct	5/22/2026	M · Option Exercise	+2.08K	—	—	6.0%	34.70K	36.77K
Common Stock Direct	5/22/2026	F · Tax Withholding	−505.00	$21.98	$11.10K	1.4%	36.77K	36.27K
Common Stock Direct	5/25/2026	M · Option Exercise	+29.00	—	—	0.1%	36.27K	36.30K
Common Stock Direct	5/25/2026	F · Tax Withholding	−7.00	$21.86	$153.02	0.0%	36.30K	36.29K
Common Stock Direct	5/25/2026	M · Option Exercise	+451.00	—	—	1.2%	36.29K	36.74K
Common Stock Direct	5/25/2026	F · Tax Withholding	−109.00	$21.86	$2.38K	0.3%	36.74K	36.63K
Common Stock Direct	5/25/2026	M · Option Exercise	+45.00	—	—	0.1%	36.63K	36.68K
Common Stock Direct	5/25/2026	F · Tax Withholding	−10.00	$21.86	$218.60	0.0%	36.68K	36.67K
Total			+5.14K		-$36.27K

Derivative Transactions6

Restricted Stock Unit (RSU)

Direct

M · Option Exercise

Converts to

Common Stock

865.00 shares

−865.00

Strike price

Held after

8.65K

Exercisable

—

5/22/2026

Restricted Stock Unit (RSU)

Direct

M · Option Exercise

Converts to

Common Stock

3.33K shares

−3.33K

Strike price

Held after

9.98K

Exercisable

—

5/22/2026

Restricted Stock Unit (RSU)

Direct

M · Option Exercise

Converts to

Common Stock

2.08K shares

−2.08K

Strike price

Held after

14.53K

Exercisable

—

5/22/2026

Restricted Stock Unit (RSU)

Direct

M · Option Exercise

Converts to

Common Stock

29.00 shares

−29.00

Strike price

Held after

115.00

Exercisable

—

5/25/2026

Restricted Stock Unit (RSU)

Direct

M · Option Exercise

Converts to

Common Stock

451.00 shares

−451.00

Strike price

Held after

2.26K

Exercisable

—

5/25/2026

Restricted Stock Unit (RSU)

Direct

M · Option Exercise

Converts to

Common Stock

45.00 shares

−45.00

Strike price

Held after

225.00

Exercisable

—

5/25/2026

Security	Converts To	Date	Type	Shares	Exercisable	Held After
Restricted Stock Unit (RSU) Direct	Common Stock865.00 shares	5/22/2026	M · Option Exercise	−865.00	—	8.65K
Restricted Stock Unit (RSU) Direct	Common Stock3.33K shares	5/22/2026	M · Option Exercise	−3.33K	—	9.98K
Restricted Stock Unit (RSU) Direct	Common Stock2.08K shares	5/22/2026	M · Option Exercise	−2.08K	—	14.53K
Restricted Stock Unit (RSU) Direct	Common Stock29.00 shares	5/25/2026	M · Option Exercise	−29.00	—	115.00
Restricted Stock Unit (RSU) Direct	Common Stock451.00 shares	5/25/2026	M · Option Exercise	−451.00	—	2.26K
Restricted Stock Unit (RSU) Direct	Common Stock45.00 shares	5/25/2026	M · Option Exercise	−45.00	—	225.00