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: 8/26/2026ACC: 0001371285-26-000189

InsiderGALLAGHER JOHN RCIK 1967117

→

IssuerTRUPANION, INC.CIK 1371285

Officer· Chief Operating Officer

Since Feb 2026

-1.65K

Net shares

Net seller

$52.4K

Total sold

Open market trades

0B · 0S

Total transactions

6.79K acquired · 8.45K disposed

Non-Derivative Transactions12

Common Stock

Direct

M · Option Exercise

+865.00

Price / share

—

Trade value

—

% of position

2.7%

8/22/2026

32.20K→33.07K

Common Stock

Direct

F · Tax Withholding

−210.00

Price / share

$31.76

Trade value

$6.67K

% of position

0.6%

8/22/2026

33.07K→32.86K

Common Stock

Direct

M · Option Exercise

+3.33K

Price / share

—

Trade value

—

% of position

10.1%

8/22/2026

32.86K→36.19K

Common Stock

Direct

F · Tax Withholding

−810.00

Price / share

$31.76

Trade value

$25.73K

% of position

2.2%

8/22/2026

36.19K→35.38K

Common Stock

Direct

M · Option Exercise

+2.08K

Price / share

—

Trade value

—

% of position

5.9%

8/22/2026

35.38K→37.45K

Common Stock

Direct

F · Tax Withholding

−505.00

Price / share

$31.76

Trade value

$16.04K

% of position

1.3%

8/22/2026

37.45K→36.95K

Common Stock

Direct

M · Option Exercise

+28.00

Price / share

—

Trade value

—

% of position

0.1%

8/25/2026

36.95K→36.98K

Common Stock

Direct

F · Tax Withholding

−6.00

Price / share

$31.84

Trade value

$191.04

% of position

0.0%

8/25/2026

36.98K→36.97K

Common Stock

Direct

M · Option Exercise

+452.00

Price / share

—

Trade value

—

% of position

1.2%

8/25/2026

36.97K→37.42K

Common Stock

Direct

F · Tax Withholding

−110.00

Price / share

$31.84

Trade value

$3.50K

% of position

0.3%

8/25/2026

37.42K→37.31K

Common Stock

Direct

M · Option Exercise

+45.00

Price / share

—

Trade value

—

% of position

0.1%

8/25/2026

37.31K→37.36K

Common Stock

Direct

F · Tax Withholding

−10.00

Price / share

$31.84

Trade value

$318.40

% of position

0.0%

8/25/2026

37.36K→37.35K

Total

Net shares

+5.14K

Net value

-$52.45K

Security	Date	Type	Shares	Price / Share	Trade Value	% of Position	Held Before	Held After
Common Stock Direct	8/22/2026	M · Option Exercise	+865.00	—	—	2.7%	32.20K	33.07K
Common Stock Direct	8/22/2026	F · Tax Withholding	−210.00	$31.76	$6.67K	0.6%	33.07K	32.86K
Common Stock Direct	8/22/2026	M · Option Exercise	+3.33K	—	—	10.1%	32.86K	36.19K
Common Stock Direct	8/22/2026	F · Tax Withholding	−810.00	$31.76	$25.73K	2.2%	36.19K	35.38K
Common Stock Direct	8/22/2026	M · Option Exercise	+2.08K	—	—	5.9%	35.38K	37.45K
Common Stock Direct	8/22/2026	F · Tax Withholding	−505.00	$31.76	$16.04K	1.3%	37.45K	36.95K
Common Stock Direct	8/25/2026	M · Option Exercise	+28.00	—	—	0.1%	36.95K	36.98K
Common Stock Direct	8/25/2026	F · Tax Withholding	−6.00	$31.84	$191.04	0.0%	36.98K	36.97K
Common Stock Direct	8/25/2026	M · Option Exercise	+452.00	—	—	1.2%	36.97K	37.42K
Common Stock Direct	8/25/2026	F · Tax Withholding	−110.00	$31.84	$3.50K	0.3%	37.42K	37.31K
Common Stock Direct	8/25/2026	M · Option Exercise	+45.00	—	—	0.1%	37.31K	37.36K
Common Stock Direct	8/25/2026	F · Tax Withholding	−10.00	$31.84	$318.40	0.0%	37.36K	37.35K
Total			+5.14K		-$52.45K

Derivative Transactions6

Restricted Stock Unit (RSU)

Direct

M · Option Exercise

Converts to

Common Stock

865.00 shares

−865.00

Strike price

Held after

7.78K

Exercisable

—

8/22/2026

Restricted Stock Unit (RSU)

Direct

M · Option Exercise

Converts to

Common Stock

3.33K shares

−3.33K

Strike price

Held after

6.66K

Exercisable

—

8/22/2026

Restricted Stock Unit (RSU)

Direct

M · Option Exercise

Converts to

Common Stock

2.08K shares

−2.08K

Strike price

Held after

12.46K

Exercisable

—

8/22/2026

Restricted Stock Unit (RSU)

Direct

M · Option Exercise

Converts to

Common Stock

28.00 shares

−28.00

Strike price

Held after

87.00

Exercisable

—

8/25/2026

Restricted Stock Unit (RSU)

Direct

M · Option Exercise

Converts to

Common Stock

452.00 shares

−452.00

Strike price

Held after

1.81K

Exercisable

—

8/25/2026

Restricted Stock Unit (RSU)

Direct

M · Option Exercise

Converts to

Common Stock

45.00 shares

−45.00

Strike price

Held after

180.00

Exercisable

—

8/25/2026

Security	Converts To	Date	Type	Shares	Exercisable	Held After
Restricted Stock Unit (RSU) Direct	Common Stock865.00 shares	8/22/2026	M · Option Exercise	−865.00	—	7.78K
Restricted Stock Unit (RSU) Direct	Common Stock3.33K shares	8/22/2026	M · Option Exercise	−3.33K	—	6.66K
Restricted Stock Unit (RSU) Direct	Common Stock2.08K shares	8/22/2026	M · Option Exercise	−2.08K	—	12.46K
Restricted Stock Unit (RSU) Direct	Common Stock28.00 shares	8/25/2026	M · Option Exercise	−28.00	—	87.00
Restricted Stock Unit (RSU) Direct	Common Stock452.00 shares	8/25/2026	M · Option Exercise	−452.00	—	1.81K
Restricted Stock Unit (RSU) Direct	Common Stock45.00 shares	8/25/2026	M · Option Exercise	−45.00	—	180.00