Trupanion Inc (TRUP) insider trading

Recent insider transactions reported to the SEC on Form 4 — directors and officers buying or selling their own company’s stock. Sourced directly from public SEC filings, latest filed Sep 30, 2026.

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Filings shown
15
Open-market buys
0
Open-market sells
7

Counts cover the 15 most recent Form 4 filings Tradune holds for TRUP (filed Jul 30 – Sep 30, 2026). No completed check of TRUP's Form 4 list on SEC EDGAR is on record yet; the latest TRUP filing Tradune holds was filed Sep 30, 2026. This is not guaranteed to be the complete record — see TRUP's full Form 4 filing history on SEC EDGAR.

Open-market activity, last 90 days

Purchases (Form 4 code P) and sales (code S) on the 15 filings Tradune holds for TRUP filed Jul 30 – Sep 30, 2026. Grants, exercises, tax withholding and the other Form 4 transaction codes are left out.

7 open-market sales by Rule 10b5-1 checkbox

On filings with the 10b5-1 box checked
5 sales· 6,444 sh
checkbox disclosed
On filings with the box not checked
2 sales· 6,602 sh
not proof that no plan exists
Not comparable
0 sales· 0 sh
filed before Apr 1, 2023, or no checkbox value in the filing data

Counts are Form 4 lines as filed. The checkbox is one per filing, so every sale on a filing with the box checked is counted there even if only some of its transactions were under a plan; it records what the filer disclosed, and the three categories are not a judgement about why a sale was made.

Open-market purchases and sales by insider
Insider Buys Sells Shares bought Shares sold Value
John R. GallagherChief Operating Officer 0 3 — 4,466 −$127,727
Margaret ToothCEO 0 3 — 2,469 −$69,044
Fawwad QureshiChief Financial Officer 0 1 — 6,111 −$183,391

Value = shares × the price reported on each Form 4 (+ purchases, − sales); every open-market line in this window disclosed a price.

Insider-activity score
0/ 100
Net insider sales
0 distinct buyers0 buy · 7 sell tx

Summarises ~90 days of public SEC Form 4 activity — more distinct buyers, officer involvement and net buying score higher. A description of filing activity, not a rating or buy signal. How this score is computed →

How to read this: an open-market purchase (Form 4 code P) is a buy at the market price with the insider’s own money, as opposed to a grant, award or option exercise; an open-market sale is code S. When two or more distinct insiders report open-market purchases in the same 90-day window, this site labels that a cluster — a definition, not a forecast; see insider cluster buying. “Held after” is Form 4 Table I column 5; “Change” = shares ÷ holdings before the trade (held after − shares for an acquisition, held after + shares for a disposition).

Insider Buying at TRUP

No open-market insider purchases (Form 4 code P) were reported for TRUP in the trailing 90 days. The filings below may include other transaction types — sales, grants, option exercises, and tax withholding — shown for completeness; they are not open-market purchases.

Recent Form 4 filings

Source: SEC EDGAR Form 4 · transaction codes explained

John R. Gallagher Chief Operating Officer · filed Sep 30, 2026 · SEC ↗
TransactionSharesPriceHeld afterChange†Date
Open-market sale 10b5-1 box checked 431 $22.92 33,311 −1.3% Sep 28, 2026

† change in this filer’s own reported holding line (Form 4 Table I, col. 5), not of total company ownership; small prior holdings produce large percentages, so under 100 shares the prior holding is shown instead.

“10b5-1 box checked” = the filer checked the Form 4 box stating that a transaction on the filing was made under a plan intended to satisfy Rule 10b5-1(c); “10b5-1 box not checked” = the box was left blank, which does not prove that no plan exists. The box applies to Form 4s filed from April 1, 2023; older filings, and boxes we could not read, carry no tag. What the 10b5-1 box means.

Margaret Tooth CEO · filed Sep 15, 2026 · SEC ↗
TransactionSharesPriceHeld afterChange†Date
Open-market sale 10b5-1 box checked 1,000 $25.00 185,952 −0.5% Sep 11, 2026
John R. Gallagher Chief Operating Officer · filed Sep 1, 2026 · SEC ↗
TransactionSharesPriceHeld afterChange†Date
Open-market sale 10b5-1 box checked 3,604 $29.70 33,742 −9.7% Aug 28, 2026
Fawwad Qureshi Chief Financial Officer · filed Aug 26, 2026 · SEC ↗
TransactionSharesPriceHeld afterChange†Date
Open-market sale 10b5-1 box not checked 6,111 $30.01 4,230 −59% Aug 26, 2026
Option exercise 3,750 — 11,838 +46% Aug 25, 2026
Tax withholding 1,497 $31.84 10,341 −13% Aug 25, 2026
Option exercise Restricted Stock Unit (RSU) 3,750 — — — Aug 25, 2026
Tax withholding 2,095 $31.76 5,423 −28% Aug 22, 2026
Option exercise 4,435 — 9,858 +82% Aug 22, 2026
Tax withholding 1,770 $31.76 8,088 −18% Aug 22, 2026
Option exercise Restricted Stock Unit (RSU) 313 — — — Aug 22, 2026
Option exercise Restricted Stock Unit (RSU) 5,248 — — — Aug 22, 2026
Option exercise Restricted Stock Unit (RSU) 4,435 — — — Aug 22, 2026
Option exercise 313 — 2,394 +15% Aug 22, 2026
Tax withholding 124 $31.76 2,270 −5.2% Aug 22, 2026
Option exercise 5,248 — 7,518 +231% Aug 22, 2026
Bradley S. Powell Director · filed Aug 26, 2026 · SEC ↗
TransactionSharesPriceHeld afterChange†Date
Option exercise Restricted Stock Unit (RSU) 1,640 — — — Aug 25, 2026
Option exercise 1,640 — 3,546 +86% Aug 22, 2026
Asher Bearman Chief Legal Officer · filed Aug 26, 2026 · SEC ↗
TransactionSharesPriceHeld afterChange†Date
Option exercise 125 — 74,053 +0.2% Aug 25, 2026
Tax withholding 40 $31.84 74,013 −0.1% Aug 25, 2026
Option exercise Restricted Stock Unit (RSU) 125 — — — Aug 25, 2026
Option exercise 265 — 72,509 +0.4% Aug 22, 2026
Tax withholding 86 $31.76 72,423 −0.1% Aug 22, 2026
Option exercise 9 — 72,432 +0.0% Aug 22, 2026
Tax withholding 2 $31.76 72,430 −0.0% Aug 22, 2026
Option exercise 379 — 72,809 +0.5% Aug 22, 2026
Tax withholding 123 $31.76 72,686 −0.2% Aug 22, 2026
Option exercise 1,832 — 74,518 +2.5% Aug 22, 2026
Tax withholding 590 $31.76 73,928 −0.8% Aug 22, 2026
Option exercise Restricted Stock Unit (RSU) 265 — — — Aug 22, 2026
Option exercise Restricted Stock Unit (RSU) 9 — — — Aug 22, 2026
Option exercise Restricted Stock Unit (RSU) 379 — — — Aug 22, 2026
Option exercise Restricted Stock Unit (RSU) 1,832 — — — Aug 22, 2026
Steve Weinrauch EVP, North Am & Vet Strategy · filed Aug 26, 2026 · SEC ↗
TransactionSharesPriceHeld afterChange†Date
Option exercise 354 — 81,826 +0.4% Aug 25, 2026
Tax withholding 86 $31.84 81,740 −0.1% Aug 25, 2026
Option exercise Restricted Stock Unit (RSU) 41 — — — Aug 25, 2026
Option exercise Restricted Stock Unit (RSU) 354 — — — Aug 25, 2026
Option exercise 41 — 81,481 +0.1% Aug 25, 2026
Tax withholding 9 $31.84 81,472 −0.0% Aug 25, 2026
Option exercise 2,931 — 80,993 +3.8% Aug 22, 2026
Tax withholding 713 $31.76 80,280 −0.9% Aug 22, 2026
Option exercise 1,533 — 81,813 +1.9% Aug 22, 2026
Tax withholding 373 $31.76 81,440 −0.5% Aug 22, 2026
Option exercise Restricted Stock Unit (RSU) 2,931 — — — Aug 22, 2026
Option exercise Restricted Stock Unit (RSU) 1,533 — — — Aug 22, 2026
Brenna McGibney Chief Administration Officer · filed Aug 26, 2026 · SEC ↗
TransactionSharesPriceHeld afterChange†Date
Option exercise 338 — 14,604 +2.4% Aug 25, 2026
Tax withholding 180 $31.84 14,424 −1.2% Aug 25, 2026
Option exercise 27 — 14,451 +0.2% Aug 25, 2026
Tax withholding 14 $31.84 14,437 −0.1% Aug 25, 2026
Option exercise Restricted Stock Unit (RSU) 234 — — — Aug 25, 2026
Option exercise Restricted Stock Unit (RSU) 31 — — — Aug 25, 2026
Option exercise Restricted Stock Unit (RSU) 17 — — — Aug 25, 2026
Option exercise Restricted Stock Unit (RSU) 338 — — — Aug 25, 2026
Option exercise Restricted Stock Unit (RSU) 27 — — — Aug 25, 2026
Option exercise 234 — 14,368 +1.7% Aug 25, 2026
Option exercise 31 — 14,274 +0.2% Aug 25, 2026
Tax withholding 125 $31.84 14,243 −0.9% Aug 25, 2026
Tax withholding 16 $31.84 14,258 −0.1% Aug 25, 2026
Option exercise 17 — 14,275 +0.1% Aug 25, 2026
Tax withholding 9 $31.84 14,266 −0.1% Aug 25, 2026
Option exercise 1,250 — 12,695 +11% Aug 22, 2026
Tax withholding 669 $31.76 12,026 −5.3% Aug 22, 2026
Option exercise 1,881 — 13,907 +16% Aug 22, 2026
Tax withholding 1,006 $31.76 12,901 −7.2% Aug 22, 2026
Option exercise 2,652 — 15,553 +21% Aug 22, 2026
Tax withholding 1,419 $31.76 14,134 −9.1% Aug 22, 2026
Option exercise Restricted Stock Unit (RSU) 1,250 — — — Aug 22, 2026
Option exercise Restricted Stock Unit (RSU) 1,881 — — — Aug 22, 2026
Option exercise Restricted Stock Unit (RSU) 2,652 — — — Aug 22, 2026
Simon Wheeler EVP, Trupanion International · filed Aug 26, 2026 · SEC ↗
TransactionSharesPriceHeld afterChange†Date
Option exercise 322 — 25,488 +1.3% Aug 25, 2026
Tax withholding 161 $31.84 25,327 −0.6% Aug 25, 2026
Option exercise Restricted Stock Unit (RSU) 322 — — — Aug 25, 2026
Option exercise 528 — 24,767 +2.2% Aug 22, 2026
Tax withholding 263 $31.76 24,504 −1.1% Aug 22, 2026
Option exercise 385 — 24,889 +1.6% Aug 22, 2026
Tax withholding 192 $31.76 24,697 −0.8% Aug 22, 2026
Option exercise 938 — 25,635 +3.8% Aug 22, 2026
Tax withholding 469 $31.76 25,166 −1.8% Aug 22, 2026
Option exercise Restricted Stock Unit (RSU) 528 — — — Aug 22, 2026
Option exercise Restricted Stock Unit (RSU) 385 — — — Aug 22, 2026
Option exercise Restricted Stock Unit (RSU) 938 — — — Aug 22, 2026
Margaret Tooth CEO · filed Aug 26, 2026 · SEC ↗
TransactionSharesPriceHeld afterChange†Date
Option exercise 1,250 — 187,443 +0.7% Aug 25, 2026
Open-market sale 10b5-1 box not checked 491 $31.84 186,952 −0.3% Aug 25, 2026
Option exercise Restricted Stock Unit (RSU) 1,250 — — — Aug 25, 2026
Option exercise 313 — 175,714 +0.2% Aug 22, 2026
Tax withholding 123 $31.76 175,591 −0.1% Aug 22, 2026
Option exercise 3,042 — 178,633 +1.7% Aug 22, 2026
Tax withholding 1,197 $31.76 177,436 −0.7% Aug 22, 2026
Option exercise 6,250 — 183,686 +3.5% Aug 22, 2026
Tax withholding 2,459 $31.76 181,227 −1.3% Aug 22, 2026
Tax withholding 3,221 $31.76 186,193 −1.7% Aug 22, 2026
Option exercise Restricted Stock Unit (RSU) 313 — — — Aug 22, 2026
Option exercise Restricted Stock Unit (RSU) 3,042 — — — Aug 22, 2026
Option exercise Restricted Stock Unit (RSU) 6,250 — — — Aug 22, 2026
Option exercise Restricted Stock Unit (RSU) 8,187 — — — Aug 22, 2026
Option exercise 8,187 — 189,414 +4.5% Aug 22, 2026
John R. Gallagher Chief Operating Officer · filed Aug 26, 2026 · SEC ↗
TransactionSharesPriceHeld afterChange†Date
Option exercise 28 — 36,975 +0.1% Aug 25, 2026
Tax withholding 6 $31.84 36,969 −0.0% Aug 25, 2026
Option exercise 452 — 37,421 +1.2% Aug 25, 2026
Tax withholding 110 $31.84 37,311 −0.3% Aug 25, 2026
Option exercise 45 — 37,356 +0.1% Aug 25, 2026
Tax withholding 10 $31.84 37,346 −0.0% Aug 25, 2026
Option exercise Restricted Stock Unit (RSU) 28 — — — Aug 25, 2026
Option exercise Restricted Stock Unit (RSU) 452 — — — Aug 25, 2026
Option exercise Restricted Stock Unit (RSU) 45 — — — Aug 25, 2026
Option exercise 865 — 33,068 +2.7% Aug 22, 2026
Tax withholding 210 $31.76 32,858 −0.6% Aug 22, 2026
Option exercise 3,328 — 36,186 +10% Aug 22, 2026
Tax withholding 810 $31.76 35,376 −2.2% Aug 22, 2026
Option exercise 2,076 — 37,452 +5.9% Aug 22, 2026
Tax withholding 505 $31.76 36,947 −1.3% Aug 22, 2026
Option exercise Restricted Stock Unit (RSU) 865 — — — Aug 22, 2026
Option exercise Restricted Stock Unit (RSU) 3,328 — — — Aug 22, 2026
Option exercise Restricted Stock Unit (RSU) 2,076 — — — Aug 22, 2026
Howard E. Rubin Director · filed Aug 26, 2026 · SEC ↗
TransactionSharesPriceHeld afterChange†Date
Option exercise 140 — 233,008 +0.1% Aug 22, 2026
Option exercise 140 — 233,148 +0.1% Aug 22, 2026
Option exercise 140 — 233,288 +0.1% Aug 22, 2026
Grant / award Restricted Stock Unit (RSU) 140 — — — Aug 22, 2026
Grant / award Restricted Stock Unit (RSU) 140 — — — Aug 22, 2026
Grant / award Restricted Stock Unit (RSU) 140 — — — Aug 22, 2026
Darryl Rawlings Director · filed Aug 26, 2026 · SEC ↗
TransactionSharesPriceHeld afterChange†Date
Option exercise 313 — 25,151 +1.3% Aug 22, 2026
Option exercise Restricted Stock Unit (RSU) 313 — — — Aug 22, 2026
Margaret Tooth CEO · filed Aug 13, 2026 · SEC ↗
TransactionSharesPriceHeld afterChange†Date
Open-market sale 10b5-1 box checked 978 $29.05 175,401 −0.6% Aug 11, 2026
John R. Gallagher Chief Operating Officer · filed Jul 30, 2026 · SEC ↗
TransactionSharesPriceHeld afterChange†Date
Open-market sale 10b5-1 box checked 431 $25.08 32,203 −1.3% Jul 28, 2026

Insider filings reported around the same time

Other companies whose most recent Form 4 was filed closest to TRUP's (Sep 30, 2026).

Frequently asked about TRUP insider activity

How many insiders bought TRUP stock in the last 90 days?

No open-market purchases (Form 4 code P) of TRUP shares were reported by Trupanion Inc insiders in the trailing 90 days. The 15 filings shown on this page cover other transaction types — sales, grants, option exercises, and tax withholding.

Who filed the most recent Form 4 for TRUP?

The most recent Form 4 on this page was filed by John R. Gallagher (Chief Operating Officer) on Sep 30, 2026, reporting 1 transaction. The original document is linked from the filing list above on SEC EDGAR. Amended filings (Form 4/A) may later revise reported figures.

What was the largest open-market TRUP insider sale shown?

The largest open-market sale among the filings shown was 6,111 TRUP shares at $30.01 (about $183,391) by Fawwad Qureshi (Chief Financial Officer) on Aug 26, 2026. Value is shares × the price reported on the Form 4; its Rule 10b5-1 box is not checked.

New to Form 4s? The transaction codes, the 90-day window and the 0–100 score are defined on the insider-activity score methodology page.

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This score summarizes SEC Form 4 filing activity over the trailing 90 days. It is descriptive, not predictive — not a rating, recommendation, or investment advice. Data: SEC EDGAR (public domain), as filed; amendments may revise figures. Tradune is not a registered investment adviser.

Data as filed; amended filings (Form 4/A) may revise figures. Sales may occur under prearranged Rule 10b5-1 trading plans.