Nasdaq · CIK 0001371285
TRUP TRUPANION, INC.
Insider trading from SEC Form 4. Last filing 13 d ago. Close $26.29 on Oct 12, 2026, +23% from the 52-week low and -40% from the high.
In brief
TRUPANION, INC. (TRUP) has 178 SEC Form 4 filings on file from 14 insiders, the latest filed on Sep 30, 2026. In the last 90 days insiders made 0 open-market buys worth $0 and 7 open-market sells worth $380k, net -$380k.
49 open-market trades have been scored at TRUP. The newest: John R Gallagher (Chief Operating Officer) sold $9,879 of stock on Sep 28, 2026, filed Sep 30, 2026, scored 0 (weak), under a 10b5-1 plan. The largest of the 49 shown: Darryl Rawlings (director) sold $2.2M on Sep 3, 2025, scored 48 (moderate). 2 insiders sold within 14 days of each other around Sep 11, 2026.
25 Form 144 notices of planned sales are on file, the latest filed Oct 9, 2026.
Last 90 days
Net insider value
-$380k
more sold than bought
Buys
0
$0 by 0 insiders
Sells
7
$380k by 3 insiders
Insiders on file
14
with a Form 4 at this company
Price and insider trades, last year
TRUPOct 12, 2026 · close 26.29
Daily candles, adjusted for splits and dividends. Green arrows are insider buys, red are sells, sized by value. Click a marked bar to open the signal.Charts by TradingView Lightweight Charts™
Signals
Open-market buys and sells at TRUPANION, INC., scored.
| Score | Insider | Value | Holdings | Price context | Filed |
|---|---|---|---|---|---|
| 0Weak | John R Gallagher Chief Operating Officer sell | $9,879 431 shares | -1% | - | |
| 18Weak | Margaret Tooth CEO sell | $25k 1,000 shares | -1% | +16% from low-45% from high | |
| 25Weak | John R Gallagher Chief Operating Officer sell | $107k 3,604 shares | -10% | +38% from low-36% from high | |
| 54Moderate | Fawwad Qureshi Chief Financial Officer sell | $183k 6,111 shares | -59% | +41% from low-35% from high | |
| 25Weak | Margaret Tooth CEO sell | $16k 491 shares | -0% | +48% from low-31% from high | |
| 18Weak | Margaret Tooth CEO sell | $28k 978 shares | -1% | +42% from low-40% from high | |
| 8Weak | John R Gallagher Chief Operating Officer sell | $11k 431 shares | -1% | +19% from low-50% from high | |
| 0Weak | John R Gallagher Chief Operating Officer sell | $11k 431 shares | -1% | +19% from low-54% from high | |
| 26Weak | Steve Weinrauch EVP, North Am & Vet Strategy sell | $147k 6,674 shares | -8% | +3% from low-61% from high | |
| 24Weak | John R Gallagher Chief Operating Officer sell | $78k 3,603 shares | -10% | +2% from low-61% from high | |
| 33Weak | Fawwad Qureshi Chief Financial Officer sell | $137k 6,177 shares | -75% | 0% from low-62% from high | |
| 25Weak | Margaret Tooth CEO sell | $11k 491 shares | -0% | +1% from low-61% from high | |
| 0Weak | John R Gallagher Chief Operating Officer sell | $12k 431 shares | -1% | +2% from low-56% from high | |
| 0Weak | John R Gallagher Chief Operating Officer sell | $11k 430 shares | -1% | +4% from low-54% from high | |
| 47Moderate | Emily Dreyer Chief Revenue Officer sell | $219k 7,792 shares | -18% | +8% from low-50% from high | |
| 31Weak | John R Gallagher Chief Operating Officer sell | $140k 5,283 shares | -14% | +3% from low-53% from high | |
| 45Moderate | Fawwad Qureshi Chief Financial Officer sell | $75k 2,837 shares | -100% | +3% from low-53% from high | |
| 32Weak | Fawwad Qureshi Chief Financial Officer sell | $119k 4,645 shares | -100% | +3% from low-53% from high | |
| 15Weak | Steve Weinrauch EVP, North Am & Vet Strategy sell | $2,270 85 shares | -0% | +3% from low-53% from high | |
| 0Weak | John R Gallagher Chief Operating Officer sell | $14k 430 shares | -1% | +1% from low-44% from high | |
| 8Weak | John R Gallagher Chief Operating Officer sell | $16k 430 shares | -1% | +16% from low-33% from high | |
| 13Weak | Margaret Tooth CEO sell | $364k 9,605 shares | -6% | +17% from low-33% from high | |
| 32Weak | John R Gallagher Chief Operating Officer sell | $222k 6,383 shares | -16% | +9% from low-37% from high | |
| 34Weak | Fawwad Qureshi Chief Financial Officer sell | $220k 6,202 shares | -100% | +8% from low-38% from high | |
| 20Weak | Margaret Tooth CEO sell | $346k 9,803 shares | -6% | +9% from low-37% from high | |
| 6Weak | Margaret Tooth CEO sell | $388k 8,884 shares | -6% | +34% from low-23% from high | |
| 15Weak | Margaret Tooth CEO sell | $124k 2,961 shares | -2% | +33% from low-24% from high | |
| 6Weak | Margaret Tooth CEO sell | $375k 8,961 shares | -6% | +33% from low-24% from high | |
| 48Moderate | Darryl Rawlings director sell | $2.2M 50,000 shares | -3% | +36% from low-22% from high | |
| 44Moderate | Fawwad Qureshi Chief Financial Officer sell | $291k 6,451 shares | -100% | +40% from low-20% from high | |
| 16Weak | Fawwad Qureshi Chief Financial Officer sell | $128k 2,800 shares | -30% | +43% from low-18% from high | |
| 45Moderate | Brenna McGibney Chief Administration Officer sell | $108k 2,390 shares | -64% | +44% from low-17% from high | |
| 25Weak | Margaret Tooth CEO sell | $9,714 200 shares | -0% | +53% from low-12% from high | |
| 52Moderate | John R Gallagher Chief Operating Officer sell | $192k 4,000 shares | -13% | +49% from low-14% from high | |
| 37Weak | Fawwad Qureshi Chief Financial Officer sell | $122k 2,534 shares | -42% | +49% from low-14% from high | |
| 28Weak | Fawwad Qureshi Chief Financial Officer sell | $38k 828 shares | -12% | +47% from low-15% from high | |
| 17Weak | Margaret Tooth CEO sell | $183k 4,000 shares | -3% | +40% from low-19% from high | |
| 60Notable | Brenna McGibney Chief Administration Officer sell | $111k 2,421 shares | -65% | +42% from low-18% from high | |
| 1Weak | Margaret Tooth CEO sell | $133k 4,000 shares | -3% | +5% from low-39% from high | |
| 35Weak | Emily Dreyer SVP, Channel Growth sell | $455k 14,025 shares | -34% | - | |
| 43Moderate | John R Gallagher Chief Operating Officer sell | $102k 3,100 shares | -11% | - | |
| 55Moderate | Fawwad Qureshi Chief Financial Officer sell | $524k 9,867 shares | -100% | - | |
| 8Weak | Fawwad Qureshi Chief Financial Officer sell | $33k 622 shares | -6% | - | |
| 47Moderate | Emily Dreyer SVP, Channel Growth sell | $219k 4,000 shares | -14% | - | |
| 55Moderate | Steve Weinrauch EVP, North Am & Vet Strategy sell | $632k 11,916 shares | -20% | - | |
| 53Moderate | Margaret Tooth CEO sell | $260k 5,000 shares | -5% | - | |
| 40Moderate | Murray B Low director sell | $105k 2,000 shares | -1% | - | |
| 43Moderate | Travis Worra General Manager sell | $105k 2,000 shares | -35% | - | |
| 25Weak | Melissa Joy Hewitt General Manager sell | $32k 1,213 shares | -20% | +31% from low-62% from high |
Planned sales
Form 144 notices filed before a sale of restricted or control stock, newest first. The sale itself usually reaches a Form 4 within days. All planned sales
| Filed | Seller | Shares | Value | Sale date | Past 3 months |
|---|---|---|---|---|---|
| Oct 9, 2026 | MARGARET R TOOTH Officer, Director | 1,000 0.00% of outstanding | $26k | Oct 9, 2026 | $53k |
| Sep 28, 2026 | JOHN GALLAGHER Officer | 431 0.00% of outstanding | $9,879 | Sep 28, 2026 | $129k |
| Sep 11, 2026 | MARGARET R TOOTH Officer, Director | 1,000 0.00% of outstanding | $25k | Sep 11, 2026 | $28k |
| Aug 28, 2026 | JOHN GALLAGHER Officer | 3,604 0.01% of outstanding | $107k | Aug 28, 2026 | $22k |
| Aug 26, 2026 | FAWWAD QURESHI Officer | 6,111 0.01% of outstanding | $183k | Aug 26, 2026 | $137k |
| Aug 11, 2026 | MARGARET R TOOTH Officer, Director | 978 0.00% of outstanding | $28k | Aug 11, 2026 | $11k |
| Jul 28, 2026 | JOHN GALLAGHER Officer | 431 0.00% of outstanding | $11k | Jul 28, 2026 | $89k |
| Jun 29, 2026 | JOHN GALLAGHER Officer | 431 0.00% of outstanding | $11k | Jun 29, 2026 | $101k |
| Jun 5, 2026 | STEVE A WEINRAUCH Officer | 6,674 0.02% of outstanding | $147k | Jun 5, 2026 | none |
| May 28, 2026 | JOHN GALLAGHER Officer | 3,603 0.01% of outstanding | $78k | May 28, 2026 | $23k |
| May 27, 2026 | FAWWAD QURESHI Officer | 6,177 0.01% of outstanding | $137k | May 27, 2026 | none |
| Apr 28, 2026 | JOHN GALLAGHER Officer | 431 0.00% of outstanding | $12k | Apr 28, 2026 | $151k |
| Mar 30, 2026 | JOHN GALLAGHER Officer | 430 0.00% of outstanding | $11k | Mar 30, 2026 | $154k |
| Mar 4, 2026 | EMILY DREYER Officer | 7,792 0.02% of outstanding | $219k | Mar 4, 2026 | none |
| Feb 27, 2026 | JOHN GALLAGHER Officer | 5,283 0.01% of outstanding | $140k | Feb 27, 2026 | $252k |
| Feb 27, 2026 | FAWWAD QURESHI Officer | 2,837 0.01% of outstanding | $75k | Feb 27, 2026 | $119k |
| Feb 25, 2026 | FAWWAD QURESHI Officer | 4,645 0.01% of outstanding | $119k | Feb 25, 2026 | $220k |
| Jan 28, 2026 | JOHN GALLAGHER Officer | 430 0.00% of outstanding | $14k | Jan 28, 2026 | $238k |
| Dec 29, 2025 | JOHN GALLAGHER Officer | 430 0.00% of outstanding | $16k | Dec 29, 2025 | $222k |
| Dec 19, 2025 | MARGARET R TOOTH Officer, Director | 9,605 0.02% of outstanding | $364k | Dec 19, 2025 | $1.1M |
| Nov 28, 2025 | JOHN GALLAGHER Officer | 6,383 0.01% of outstanding | $222k | Nov 28, 2025 | none |
| Nov 26, 2025 | FAWWAD QURESHI Officer | 6,202 0.01% of outstanding | $220k | Nov 26, 2025 | $419k |
| Nov 25, 2025 | MARGARET R TOOTH Officer, Director | 9,803 0.02% of outstanding | $346k | Nov 25, 2025 | $764k |
| Oct 27, 2025 | MARGARET TOOTH Officer, Director | 8,884 0.02% of outstanding | $388k | Oct 27, 2025 | $375k |
| Sep 25, 2025 | MARGARET TOOTH Officer, Director | 8,961 0.02% of outstanding | $375k | Sep 25, 2025 | none |
Transactions
The newest 50 of 1,173 rows filed, every code.
| Date | Insider | Transaction | Shares | Price | Value | Holdings after | Filed |
|---|---|---|---|---|---|---|---|
| Sep 28, 2026 | John R Gallagher Chief Operating Officer | SOpen-market sale Common Stock10b5-1 | -431 | $22.92 | $9,879 | 33,311 | 13 d ago |
| Sep 11, 2026 | Margaret Tooth CEO | SOpen-market sale Common Stock10b5-1 | -1,000 | $25.00 | $25k | 185,952 | 28 d ago |
| Aug 28, 2026 | John R Gallagher Chief Operating Officer | SOpen-market sale Common Stock10b5-1 | -3,604 | $29.70 | $107k | 33,742 | 42 d ago |
| Aug 22, 2026 | Asher Bearman Chief Legal Officer | MOption exercise Common Stock | +265 | - | - | 72,509 | Aug 26, 2026 |
| Aug 22, 2026 | Simon Wheeler EVP, Trupanion International | MOption exercise Common Stock | +528 | - | - | 24,767 | Aug 26, 2026 |
| Aug 22, 2026 | Howard E Rubin director | MOption exercise Common Stock | +140 | - | - | 233,008 | Aug 26, 2026 |
| Aug 22, 2026 | Bradley S Powell director | MOption exercise Common Stock | +1,640 | - | - | 3,546 | Aug 26, 2026 |
| Aug 22, 2026 | Margaret Tooth CEO | MOption exercise Common Stock | +313 | - | - | 175,714 | Aug 26, 2026 |
| Aug 22, 2026 | Darryl Rawlings director | MOption exercise Common Stock | +313 | - | - | 25,151 | Aug 26, 2026 |
| Aug 22, 2026 | John R Gallagher Chief Operating Officer | MOption exercise Common Stock | +865 | - | - | 33,068 | Aug 26, 2026 |
| Aug 22, 2026 | Steve Weinrauch EVP, North Am & Vet Strategy | MOption exercise Common Stock | +2,931 | - | - | 80,993 | Aug 26, 2026 |
| Aug 22, 2026 | Fawwad Qureshi Chief Financial Officer | MOption exercise Common Stock | +313 | - | - | 2,394 | Aug 26, 2026 |
| Aug 22, 2026 | Brenna McGibney Chief Administration Officer | MOption exercise Common Stock | +1,250 | - | - | 12,695 | Aug 26, 2026 |
| Aug 25, 2026 | Bradley S Powell director | MOption exercise Restricted Stock Unit (RSU)derivative | -1,640 | $0.00 | $0 | 4,923 | Aug 26, 2026 |
| Aug 22, 2026 | Howard E Rubin director | MOption exercise Common Stock | +140 | - | - | 233,148 | Aug 26, 2026 |
| Aug 22, 2026 | Brenna McGibney Chief Administration Officer | FTax withholding Common Stock | -669 | $31.76 | $21k | 12,026 | Aug 26, 2026 |
| Aug 22, 2026 | Darryl Rawlings director | MOption exercise Restricted Stock Unit (RSU)derivative | -313 | $0.00 | $0 | 1,875 | Aug 26, 2026 |
| Aug 22, 2026 | Simon Wheeler EVP, Trupanion International | FTax withholding Common Stock | -263 | $31.76 | $8,353 | 24,504 | Aug 26, 2026 |
| Aug 22, 2026 | Steve Weinrauch EVP, North Am & Vet Strategy | FTax withholding Common Stock | -713 | $31.76 | $23k | 80,280 | Aug 26, 2026 |
| Aug 22, 2026 | John R Gallagher Chief Operating Officer | FTax withholding Common Stock | -210 | $31.76 | $6,670 | 32,858 | Aug 26, 2026 |
| Aug 22, 2026 | Fawwad Qureshi Chief Financial Officer | FTax withholding Common Stock | -124 | $31.76 | $3,938 | 2,270 | Aug 26, 2026 |
| Aug 22, 2026 | Margaret Tooth CEO | FTax withholding Common Stock | -123 | $31.76 | $3,906 | 175,591 | Aug 26, 2026 |
| Aug 22, 2026 | Asher Bearman Chief Legal Officer | FTax withholding Common Stock | -86 | $31.76 | $2,731 | 72,423 | Aug 26, 2026 |
| Aug 22, 2026 | Steve Weinrauch EVP, North Am & Vet Strategy | MOption exercise Common Stock | +1,533 | - | - | 81,813 | Aug 26, 2026 |
| Aug 22, 2026 | Margaret Tooth CEO | MOption exercise Common Stock | +3,042 | - | - | 178,633 | Aug 26, 2026 |
| Aug 22, 2026 | Howard E Rubin director | MOption exercise Common Stock | +140 | - | - | 233,288 | Aug 26, 2026 |
| Aug 22, 2026 | Fawwad Qureshi Chief Financial Officer | MOption exercise Common Stock | +5,248 | - | - | 7,518 | Aug 26, 2026 |
| Aug 22, 2026 | Simon Wheeler EVP, Trupanion International | MOption exercise Common Stock | +385 | - | - | 24,889 | Aug 26, 2026 |
| Aug 22, 2026 | Brenna McGibney Chief Administration Officer | MOption exercise Common Stock | +1,881 | - | - | 13,907 | Aug 26, 2026 |
| Aug 22, 2026 | John R Gallagher Chief Operating Officer | MOption exercise Common Stock | +3,328 | - | - | 36,186 | Aug 26, 2026 |
| Aug 22, 2026 | Asher Bearman Chief Legal Officer | MOption exercise Common Stock | +9 | - | - | 72,432 | Aug 26, 2026 |
| Aug 22, 2026 | Steve Weinrauch EVP, North Am & Vet Strategy | FTax withholding Common Stock | -373 | $31.76 | $12k | 81,440 | Aug 26, 2026 |
| Aug 22, 2026 | Margaret Tooth CEO | FTax withholding Common Stock | -1,197 | $31.76 | $38k | 177,436 | Aug 26, 2026 |
| Aug 22, 2026 | Fawwad Qureshi Chief Financial Officer | FTax withholding Common Stock | -2,095 | $31.76 | $67k | 5,423 | Aug 26, 2026 |
| Aug 22, 2026 | John R Gallagher Chief Operating Officer | FTax withholding Common Stock | -810 | $31.76 | $26k | 35,376 | Aug 26, 2026 |
| Aug 22, 2026 | Brenna McGibney Chief Administration Officer | FTax withholding Common Stock | -1,006 | $31.76 | $32k | 12,901 | Aug 26, 2026 |
| Aug 22, 2026 | Simon Wheeler EVP, Trupanion International | FTax withholding Common Stock | -192 | $31.76 | $6,098 | 24,697 | Aug 26, 2026 |
| Aug 22, 2026 | Howard E Rubin director | AGrant or award Restricted Stock Unit (RSU)derivative | -140 | $0.00 | $0 | 422 | Aug 26, 2026 |
| Aug 22, 2026 | Asher Bearman Chief Legal Officer | FTax withholding Common Stock | -2 | $31.76 | $64 | 72,430 | Aug 26, 2026 |
| Aug 22, 2026 | Margaret Tooth CEO | MOption exercise Common Stock | +6,250 | - | - | 183,686 | Aug 26, 2026 |
| Aug 22, 2026 | Fawwad Qureshi Chief Financial Officer | MOption exercise Common Stock | +4,435 | - | - | 9,858 | Aug 26, 2026 |
| Aug 25, 2026 | Steve Weinrauch EVP, North Am & Vet Strategy | MOption exercise Common Stock | +41 | - | - | 81,481 | Aug 26, 2026 |
| Aug 22, 2026 | Howard E Rubin director | AGrant or award Restricted Stock Unit (RSU)derivative | -140 | $0.00 | $0 | 422 | Aug 26, 2026 |
| Aug 22, 2026 | John R Gallagher Chief Operating Officer | MOption exercise Common Stock | +2,076 | - | - | 37,452 | Aug 26, 2026 |
| Aug 22, 2026 | Simon Wheeler EVP, Trupanion International | MOption exercise Common Stock | +938 | - | - | 25,635 | Aug 26, 2026 |
| Aug 22, 2026 | Brenna McGibney Chief Administration Officer | MOption exercise Common Stock | +2,652 | - | - | 15,553 | Aug 26, 2026 |
| Aug 22, 2026 | Asher Bearman Chief Legal Officer | MOption exercise Common Stock | +379 | - | - | 72,809 | Aug 26, 2026 |
| Aug 22, 2026 | Margaret Tooth CEO | FTax withholding Common Stock | -2,459 | $31.76 | $78k | 181,227 | Aug 26, 2026 |
| Aug 22, 2026 | Howard E Rubin director | AGrant or award Restricted Stock Unit (RSU)derivative | -140 | $0.00 | $0 | 422 | Aug 26, 2026 |
| Aug 25, 2026 | Steve Weinrauch EVP, North Am & Vet Strategy | FTax withholding Common Stock | -9 | $31.84 | $287 | 81,472 | Aug 26, 2026 |
50 of 1,173 rows shown.
Insiders
Everyone who has filed a Form 4 here.
- Asher BearmanChief Legal Officer
- Emily DreyerSVP, Channel Growth
- John R GallagherEVP, Global Support Services
- Melissa Joy HewittGeneral Manager
- Murray B Lowdirector
- Brenna McGibneyChief Administration Officer
- Bradley S Powellcfo, officer, director
- Fawwad QureshiChief Financial Officer
- Darryl Rawlingsdirector
- Howard E Rubindirector
- Margaret ToothCEO
- Steve WeinrauchEVP, North Am & Vet Strategy
- Simon WheelerEVP, Trupanion International
- Travis WorraGeneral Manager
Questions about TRUP
Answered from the filings on this page, as of the latest one.
Are insiders buying TRUP?
As of Sep 30, 2026, SEC Form 4 filings show 0 open-market buys worth $0 by 0 insiders and 7 open-market sells worth $380k by 3 insiders at TRUPANION, INC. in the last 90 days, net -$380k. Only purchases (code P) and sales (code S) count; grants, option exercises and tax withholding do not.
Who was the last insider to trade TRUP on the open market?
John R Gallagher (Chief Operating Officer) sold $9,879 of TRUP on Sep 28, 2026 and filed the Form 4 on Sep 30, 2026. InsiderTell scored 0 (weak), under a 10b5-1 plan.
How many insiders file Form 4 at TRUPANION, INC.?
14 people have filed a Form 4 at TRUPANION, INC., among them Asher Bearman (Chief Legal Officer), Emily Dreyer (SVP, Channel Growth), John R Gallagher (EVP, Global Support Services). Officers, directors and holders of more than 10% of a share class must report their trades within two business days.
Not investment advice. Scores and forward returns are decision support built from public SEC filings and past prices; they describe what happened after comparable filings, not what will happen after this one. Do your own research and size your risk.