Form 4
Open-market sale
Insider Selling
2026-10-13
TRUP insider Tooth Margaret (Director, CEO) sold 1,000 shares (~$25.8K)
Tooth Margaret, listed as Director, CEO at TRUPANION, INC., reported an open-market sale of 1,000 TRUP shares in a Form 4 filing. This is a confirmed insider sale, not just a proposed sale notice.
The insider sold shares on the open market. Sales may be discretionary or executed automatically under a pre-arranged Rule 10b5-1 trading plan, and a Form 4 does not always make clear which applies.
Transactions reported on this filing
| Code |
Nature |
Shares |
Price |
Value |
S |
Open-market sale
|
1,000 |
$25.84 |
$25.8K |
Filing: Form 4 (Insider Transaction)
Insider: Tooth Margaret (Director, CEO)
Shares: 1,000
Est. Value: $25.8K
Form 4
Open-market sale
Insider Selling
2026-09-30
TRUP insider GALLAGHER JOHN R (Chief Operating Officer) sold 431 shares (~$9.9K)
GALLAGHER JOHN R, listed as Chief Operating Officer at TRUPANION, INC., reported an open-market sale of 431 TRUP shares in a Form 4 filing. This is a confirmed insider sale, not just a proposed sale notice.
The insider sold shares on the open market. Sales may be discretionary or executed automatically under a pre-arranged Rule 10b5-1 trading plan, and a Form 4 does not always make clear which applies.
Transactions reported on this filing
| Code |
Nature |
Shares |
Price |
Value |
S |
Open-market sale
|
431 |
$22.92 |
$9.9K |
Filing: Form 4 (Insider Transaction)
Insider: GALLAGHER JOHN R (Chief Operating Officer)
Shares: 431
Est. Value: $9.9K
Form 4
Open-market sale
Insider Selling
2026-09-15
TRUP insider Tooth Margaret (Director, CEO) sold 1,000 shares (~$25.0K)
Tooth Margaret, listed as Director, CEO at TRUPANION, INC., reported an open-market sale of 1,000 TRUP shares in a Form 4 filing. This is a confirmed insider sale, not just a proposed sale notice.
The insider sold shares on the open market. Sales may be discretionary or executed automatically under a pre-arranged Rule 10b5-1 trading plan, and a Form 4 does not always make clear which applies.
Transactions reported on this filing
| Code |
Nature |
Shares |
Price |
Value |
S |
Open-market sale
|
1,000 |
$25.00 |
$25.0K |
Filing: Form 4 (Insider Transaction)
Insider: Tooth Margaret (Director, CEO)
Shares: 1,000
Est. Value: $25.0K
Form 4
Open-market sale
Insider Selling
2026-09-01
TRUP insider GALLAGHER JOHN R (Chief Operating Officer) sold 3,604 shares (~$107.0K)
GALLAGHER JOHN R, listed as Chief Operating Officer at TRUPANION, INC., reported an open-market sale of 3,604 TRUP shares in a Form 4 filing. This is a confirmed insider sale, not just a proposed sale notice.
The insider sold shares on the open market. Sales may be discretionary or executed automatically under a pre-arranged Rule 10b5-1 trading plan, and a Form 4 does not always make clear which applies.
Transactions reported on this filing
| Code |
Nature |
Shares |
Price |
Value |
S |
Open-market sale
|
3,604 |
$29.70 |
$107.0K |
Filing: Form 4 (Insider Transaction)
Insider: GALLAGHER JOHN R (Chief Operating Officer)
Shares: 3,604
Est. Value: $107.0K
Form 4
Compensation award
Tax / Compensation Filing
2026-08-26
TRUP insider Form 4 filed for equity award, exercise, or tax withholding
RUBIN HOWARD E (Director) filed a Form 4 covering compensation-related activity such as stock awards, option exercises, conversions, or tax withholding. These filings are usually neutral.
Shares were granted as compensation rather than purchased. No cash changed hands, so the filing reflects a pay decision by the company, not a judgement about the price.
Transactions reported on this filing
| Code |
Nature |
Shares |
Price |
Value |
M |
Option exercise
|
140 |
— |
— |
M |
Option exercise
|
140 |
— |
— |
M |
Option exercise
|
140 |
— |
— |
A |
Compensation award
derivative · Restricted Stock Unit (RSU)
|
140 |
— |
— |
A |
Compensation award
derivative · Restricted Stock Unit (RSU)
|
140 |
— |
— |
A |
Compensation award
derivative · Restricted Stock Unit (RSU)
|
140 |
— |
— |
Filing: Form 4 (Insider Transaction)
Insider: RUBIN HOWARD E (Director)
Shares: 420
Form 4
Option exercise
Tax / Compensation Filing
2026-08-26
TRUP insider Form 4 filed for equity award, exercise, or tax withholding
POWELL BRADLEY S (Director) filed a Form 4 covering compensation-related activity such as stock awards, option exercises, conversions, or tax withholding. These filings are usually neutral.
The insider converted options into shares. The exercise price was fixed when the options were granted, so the timing usually tracks an expiry schedule.
Transactions reported on this filing
| Code |
Nature |
Shares |
Price |
Value |
M |
Option exercise
|
1,640 |
— |
— |
M |
Option exercise
derivative · Restricted Stock Unit (RSU)
|
1,640 |
— |
— |
Filing: Form 4 (Insider Transaction)
Insider: POWELL BRADLEY S (Director)
Shares: 1,640
Form 4
Option exercise
Tax / Compensation Filing
2026-08-26
TRUP insider Form 4 filed for equity award, exercise, or tax withholding
BEARMAN ASHER (Chief Legal Officer) filed a Form 4 covering compensation-related activity such as stock awards, option exercises, conversions, or tax withholding. These filings are usually neutral.
The insider converted options into shares. The exercise price was fixed when the options were granted, so the timing usually tracks an expiry schedule.
Transactions reported on this filing
| Code |
Nature |
Shares |
Price |
Value |
M |
Option exercise
|
265 |
— |
— |
F |
Tax withholding on vested shares
|
86 |
$31.76 |
$2.7K |
M |
Option exercise
|
9 |
— |
— |
F |
Tax withholding on vested shares
|
2 |
$31.76 |
$63.52 |
M |
Option exercise
|
379 |
— |
— |
F |
Tax withholding on vested shares
|
123 |
$31.76 |
$3.9K |
M |
Option exercise
|
1,832 |
— |
— |
F |
Tax withholding on vested shares
|
590 |
$31.76 |
$18.7K |
M |
Option exercise
|
125 |
— |
— |
F |
Tax withholding on vested shares
|
40 |
$31.84 |
$1.3K |
M |
Option exercise
derivative · Restricted Stock Unit (RSU)
|
265 |
— |
— |
M |
Option exercise
derivative · Restricted Stock Unit (RSU)
|
9 |
— |
— |
M |
Option exercise
derivative · Restricted Stock Unit (RSU)
|
379 |
— |
— |
M |
Option exercise
derivative · Restricted Stock Unit (RSU)
|
1,832 |
— |
— |
M |
Option exercise
derivative · Restricted Stock Unit (RSU)
|
125 |
— |
— |
Filing: Form 4 (Insider Transaction)
Insider: BEARMAN ASHER (Chief Legal Officer)
Shares: 3,451
Form 4
Option exercise
Tax / Compensation Filing
2026-08-26
TRUP insider Form 4 filed for equity award, exercise, or tax withholding
WEINRAUCH STEVE (EVP, North Am & Vet Strategy) filed a Form 4 covering compensation-related activity such as stock awards, option exercises, conversions, or tax withholding. These filings are usually neutral.
The insider converted options into shares. The exercise price was fixed when the options were granted, so the timing usually tracks an expiry schedule.
Transactions reported on this filing
| Code |
Nature |
Shares |
Price |
Value |
M |
Option exercise
|
2,931 |
— |
— |
F |
Tax withholding on vested shares
|
713 |
$31.76 |
$22.6K |
M |
Option exercise
|
1,533 |
— |
— |
F |
Tax withholding on vested shares
|
373 |
$31.76 |
$11.8K |
M |
Option exercise
|
41 |
— |
— |
F |
Tax withholding on vested shares
|
9 |
$31.84 |
$286.56 |
M |
Option exercise
|
354 |
— |
— |
F |
Tax withholding on vested shares
|
86 |
$31.84 |
$2.7K |
M |
Option exercise
derivative · Restricted Stock Unit (RSU)
|
2,931 |
— |
— |
M |
Option exercise
derivative · Restricted Stock Unit (RSU)
|
1,533 |
— |
— |
M |
Option exercise
derivative · Restricted Stock Unit (RSU)
|
41 |
— |
— |
M |
Option exercise
derivative · Restricted Stock Unit (RSU)
|
354 |
— |
— |
Filing: Form 4 (Insider Transaction)
Insider: WEINRAUCH STEVE (EVP, North Am & Vet Strategy)
Shares: 6,040
Form 4
Option exercise
Tax / Compensation Filing
2026-08-26
TRUP insider Form 4 filed for equity award, exercise, or tax withholding
MCGIBNEY BRENNA (Chief Administration Officer) filed a Form 4 covering compensation-related activity such as stock awards, option exercises, conversions, or tax withholding. These filings are usually neutral.
The insider converted options into shares. The exercise price was fixed when the options were granted, so the timing usually tracks an expiry schedule.
Transactions reported on this filing
| Code |
Nature |
Shares |
Price |
Value |
M |
Option exercise
|
1,250 |
— |
— |
F |
Tax withholding on vested shares
|
669 |
$31.76 |
$21.2K |
M |
Option exercise
|
1,881 |
— |
— |
F |
Tax withholding on vested shares
|
1,006 |
$31.76 |
$32.0K |
M |
Option exercise
|
2,652 |
— |
— |
F |
Tax withholding on vested shares
|
1,419 |
$31.76 |
$45.1K |
M |
Option exercise
|
234 |
— |
— |
F |
Tax withholding on vested shares
|
125 |
$31.84 |
$4.0K |
M |
Option exercise
|
31 |
— |
— |
F |
Tax withholding on vested shares
|
16 |
$31.84 |
$509.44 |
M |
Option exercise
|
17 |
— |
— |
F |
Tax withholding on vested shares
|
9 |
$31.84 |
$286.56 |
M |
Option exercise
|
338 |
— |
— |
F |
Tax withholding on vested shares
|
180 |
$31.84 |
$5.7K |
M |
Option exercise
|
27 |
— |
— |
F |
Tax withholding on vested shares
|
14 |
$31.84 |
$445.76 |
M |
Option exercise
derivative · Restricted Stock Unit (RSU)
|
1,250 |
— |
— |
M |
Option exercise
derivative · Restricted Stock Unit (RSU)
|
1,881 |
— |
— |
M |
Option exercise
derivative · Restricted Stock Unit (RSU)
|
2,652 |
— |
— |
M |
Option exercise
derivative · Restricted Stock Unit (RSU)
|
234 |
— |
— |
M |
Option exercise
derivative · Restricted Stock Unit (RSU)
|
31 |
— |
— |
M |
Option exercise
derivative · Restricted Stock Unit (RSU)
|
17 |
— |
— |
M |
Option exercise
derivative · Restricted Stock Unit (RSU)
|
338 |
— |
— |
M |
Option exercise
derivative · Restricted Stock Unit (RSU)
|
27 |
— |
— |
Filing: Form 4 (Insider Transaction)
Insider: MCGIBNEY BRENNA (Chief Administration Officer)
Shares: 9,868
Form 4
Option exercise
Tax / Compensation Filing
2026-08-26
TRUP insider Form 4 filed for equity award, exercise, or tax withholding
WHEELER SIMON (EVP, Trupanion International) filed a Form 4 covering compensation-related activity such as stock awards, option exercises, conversions, or tax withholding. These filings are usually neutral.
The insider converted options into shares. The exercise price was fixed when the options were granted, so the timing usually tracks an expiry schedule.
Transactions reported on this filing
| Code |
Nature |
Shares |
Price |
Value |
M |
Option exercise
|
528 |
— |
— |
F |
Tax withholding on vested shares
|
263 |
$31.76 |
$8.4K |
M |
Option exercise
|
385 |
— |
— |
F |
Tax withholding on vested shares
|
192 |
$31.76 |
$6.1K |
M |
Option exercise
|
938 |
— |
— |
F |
Tax withholding on vested shares
|
469 |
$31.76 |
$14.9K |
M |
Option exercise
|
322 |
— |
— |
F |
Tax withholding on vested shares
|
161 |
$31.84 |
$5.1K |
M |
Option exercise
derivative · Restricted Stock Unit (RSU)
|
528 |
— |
— |
M |
Option exercise
derivative · Restricted Stock Unit (RSU)
|
385 |
— |
— |
M |
Option exercise
derivative · Restricted Stock Unit (RSU)
|
938 |
— |
— |
M |
Option exercise
derivative · Restricted Stock Unit (RSU)
|
322 |
— |
— |
Filing: Form 4 (Insider Transaction)
Insider: WHEELER SIMON (EVP, Trupanion International)
Shares: 3,258
Form 4
Open-market sale
Insider Selling
2026-08-26
TRUP insider Qureshi Fawwad (Chief Financial Officer) sold 6,111 shares (~$183.4K)
Qureshi Fawwad, listed as Chief Financial Officer at TRUPANION, INC., reported an open-market sale of 6,111 TRUP shares in a Form 4 filing. This is a confirmed insider sale, not just a proposed sale notice.
The insider sold shares on the open market. Sales may be discretionary or executed automatically under a pre-arranged Rule 10b5-1 trading plan, and a Form 4 does not always make clear which applies.
Transactions reported on this filing
| Code |
Nature |
Shares |
Price |
Value |
M |
Option exercise
|
313 |
— |
— |
F |
Tax withholding on vested shares
|
124 |
$31.76 |
$3.9K |
M |
Option exercise
|
5,248 |
— |
— |
F |
Tax withholding on vested shares
|
2,095 |
$31.76 |
$66.5K |
M |
Option exercise
|
4,435 |
— |
— |
F |
Tax withholding on vested shares
|
1,770 |
$31.76 |
$56.2K |
M |
Option exercise
|
3,750 |
— |
— |
F |
Tax withholding on vested shares
|
1,497 |
$31.84 |
$47.7K |
S |
Open-market sale
|
6,111 |
$30.01 |
$183.4K |
M |
Option exercise
derivative · Restricted Stock Unit (RSU)
|
313 |
— |
— |
M |
Option exercise
derivative · Restricted Stock Unit (RSU)
|
5,248 |
— |
— |
M |
Option exercise
derivative · Restricted Stock Unit (RSU)
|
4,435 |
— |
— |
M |
Option exercise
derivative · Restricted Stock Unit (RSU)
|
3,750 |
— |
— |
Filing: Form 4 (Insider Transaction)
Insider: Qureshi Fawwad (Chief Financial Officer)
Shares: 6,111
Est. Value: $183.4K
Form 4
Open-market sale
Insider Selling
2026-08-26
TRUP insider Tooth Margaret (Director, CEO) sold 491 shares (~$15.6K)
Tooth Margaret, listed as Director, CEO at TRUPANION, INC., reported an open-market sale of 491 TRUP shares in a Form 4 filing. This is a confirmed insider sale, not just a proposed sale notice.
The insider sold shares on the open market. Sales may be discretionary or executed automatically under a pre-arranged Rule 10b5-1 trading plan, and a Form 4 does not always make clear which applies.
Transactions reported on this filing
| Code |
Nature |
Shares |
Price |
Value |
M |
Option exercise
|
313 |
— |
— |
F |
Tax withholding on vested shares
|
123 |
$31.76 |
$3.9K |
M |
Option exercise
|
3,042 |
— |
— |
F |
Tax withholding on vested shares
|
1,197 |
$31.76 |
$38.0K |
M |
Option exercise
|
6,250 |
— |
— |
F |
Tax withholding on vested shares
|
2,459 |
$31.76 |
$78.1K |
M |
Option exercise
|
8,187 |
— |
— |
F |
Tax withholding on vested shares
|
3,221 |
$31.76 |
$102.3K |
M |
Option exercise
|
1,250 |
— |
— |
S |
Open-market sale
|
491 |
$31.84 |
$15.6K |
M |
Option exercise
derivative · Restricted Stock Unit (RSU)
|
313 |
— |
— |
M |
Option exercise
derivative · Restricted Stock Unit (RSU)
|
3,042 |
— |
— |
M |
Option exercise
derivative · Restricted Stock Unit (RSU)
|
6,250 |
— |
— |
M |
Option exercise
derivative · Restricted Stock Unit (RSU)
|
8,187 |
— |
— |
M |
Option exercise
derivative · Restricted Stock Unit (RSU)
|
1,250 |
— |
— |
Filing: Form 4 (Insider Transaction)
Insider: Tooth Margaret (Director, CEO)
Shares: 491
Est. Value: $15.6K
Form 4
Option exercise
Tax / Compensation Filing
2026-08-26
TRUP insider Form 4 filed for equity award, exercise, or tax withholding
GALLAGHER JOHN R (Chief Operating Officer) filed a Form 4 covering compensation-related activity such as stock awards, option exercises, conversions, or tax withholding. These filings are usually neutral.
The insider converted options into shares. The exercise price was fixed when the options were granted, so the timing usually tracks an expiry schedule.
Transactions reported on this filing
| Code |
Nature |
Shares |
Price |
Value |
M |
Option exercise
|
865 |
— |
— |
F |
Tax withholding on vested shares
|
210 |
$31.76 |
$6.7K |
M |
Option exercise
|
3,328 |
— |
— |
F |
Tax withholding on vested shares
|
810 |
$31.76 |
$25.7K |
M |
Option exercise
|
2,076 |
— |
— |
F |
Tax withholding on vested shares
|
505 |
$31.76 |
$16.0K |
M |
Option exercise
|
28 |
— |
— |
F |
Tax withholding on vested shares
|
6 |
$31.84 |
$191.04 |
M |
Option exercise
|
452 |
— |
— |
F |
Tax withholding on vested shares
|
110 |
$31.84 |
$3.5K |
M |
Option exercise
|
45 |
— |
— |
F |
Tax withholding on vested shares
|
10 |
$31.84 |
$318.40 |
M |
Option exercise
derivative · Restricted Stock Unit (RSU)
|
865 |
— |
— |
M |
Option exercise
derivative · Restricted Stock Unit (RSU)
|
3,328 |
— |
— |
M |
Option exercise
derivative · Restricted Stock Unit (RSU)
|
2,076 |
— |
— |
M |
Option exercise
derivative · Restricted Stock Unit (RSU)
|
28 |
— |
— |
M |
Option exercise
derivative · Restricted Stock Unit (RSU)
|
452 |
— |
— |
M |
Option exercise
derivative · Restricted Stock Unit (RSU)
|
45 |
— |
— |
Filing: Form 4 (Insider Transaction)
Insider: GALLAGHER JOHN R (Chief Operating Officer)
Shares: 8,445
Form 4
Option exercise
Tax / Compensation Filing
2026-08-26
TRUP insider Form 4 filed for equity award, exercise, or tax withholding
RAWLINGS DARRYL (Director) filed a Form 4 covering compensation-related activity such as stock awards, option exercises, conversions, or tax withholding. These filings are usually neutral.
The insider converted options into shares. The exercise price was fixed when the options were granted, so the timing usually tracks an expiry schedule.
Transactions reported on this filing
| Code |
Nature |
Shares |
Price |
Value |
M |
Option exercise
|
313 |
— |
— |
M |
Option exercise
derivative · Restricted Stock Unit (RSU)
|
313 |
— |
— |
Filing: Form 4 (Insider Transaction)
Insider: RAWLINGS DARRYL (Director)
Shares: 313
Form 4
Open-market sale
Insider Selling
2026-08-13
TRUP insider Tooth Margaret (Director, CEO) sold 978 shares (~$28.4K)
Tooth Margaret, listed as Director, CEO at TRUPANION, INC., reported an open-market sale of 978 TRUP shares in a Form 4 filing. This is a confirmed insider sale, not just a proposed sale notice.
The insider sold shares on the open market. Sales may be discretionary or executed automatically under a pre-arranged Rule 10b5-1 trading plan, and a Form 4 does not always make clear which applies.
Transactions reported on this filing
| Code |
Nature |
Shares |
Price |
Value |
S |
Open-market sale
|
978 |
$29.05 |
$28.4K |
Filing: Form 4 (Insider Transaction)
Insider: Tooth Margaret (Director, CEO)
Shares: 978
Est. Value: $28.4K