Insider · CIK 0001611679
Darryl Rawlings
Files at TRUP (TRUPANION, INC.). First filing Sep 5, 2025, latest Sep 5, 2025.
In brief
Darryl Rawlings files SEC Form 4 as director and CEO at TRUP (TRUPANION, INC.). Since Sep 5, 2025, Darryl Rawlings has reported 0 open-market buys worth $0 and 1 open-market sell worth $2.2M, the latest filed on Sep 5, 2025.
A track record needs three past buys with six months of prices behind them; Darryl Rawlings has 0, so none is measured yet.
The newest scored trade: sold $2.2M of TRUP on Sep 3, 2025, filed Sep 5, 2025, scored 48 (moderate).
Where the trades landed
Last year at the company this insider has traded most, with each buy and sell on the bar it happened.
TRUP: TRUPANION, INC.
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
This insider’s open-market buys and sells, scored.
| Score | Company | Value | Holdings | Price context | Filed |
|---|---|---|---|---|---|
| 48Moderate | TRUPANION, INC. | $2.2M 50,000 shares | -3% | +36% from low-22% from high |
Planned sales
Form 144 notices this insider filed before selling restricted or control stock, newest first.
| Filed | Company | Shares | Value | Sale date | Past 3 months |
|---|---|---|---|---|---|
| Sep 4, 2025 | TRUP TRUPANION, INC. | 30,369 0.07% of outstanding | $136k | Sep 4, 2025 | $878k |
| Sep 3, 2025 | TRUP TRUPANION, INC. | 19,631 0.05% of outstanding | $878k | Sep 3, 2025 | none |
| May 16, 2025 | TRUP TRUPANION, INC. | 24,000 0.06% of outstanding | $1.1M | May 16, 2025 | $135k |
| Mar 5, 2025 | TRUP TRUPANION, INC. | 4,000 0.01% of outstanding | $134k | Mar 5, 2025 | none |
Transactions
The newest 50 of 66 rows this insider has filed.
| Date | Company | Transaction | Shares | Price | Value | Holdings after | Filed |
|---|---|---|---|---|---|---|---|
| Aug 22, 2026 | TRUP TRUPANION, INC. | MOption exercise Common Stock | +313 | - | - | 25,151 | Aug 26, 2026 |
| Aug 22, 2026 | TRUP TRUPANION, INC. | MOption exercise Restricted Stock Unit (RSU)derivative | -313 | $0.00 | $0 | 1,875 | Aug 26, 2026 |
| May 22, 2026 | TRUP TRUPANION, INC. | MOption exercise Common Stock | +312 | - | - | 24,838 | May 27, 2026 |
| May 22, 2026 | TRUP TRUPANION, INC. | MOption exercise Restricted Stock Unit (RSU)derivative | -312 | $0.00 | $0 | 2,188 | May 27, 2026 |
| May 6, 2026 | TRUP TRUPANION, INC. | JOther Common Stockindirect: By Kuyashii Primary Equities LLC | +1,359 | - | - | 1,435,340 | May 8, 2026 |
| Feb 25, 2026 | TRUP TRUPANION, INC. | MOption exercise Common Stock | +946 | - | - | 42,232 | Feb 27, 2026 |
| Feb 25, 2026 | TRUP TRUPANION, INC. | MOption exercise Restricted Stock Unit (RSU)derivative | -946 | $0.00 | $0 | 0 | Feb 27, 2026 |
| Feb 22, 2026 | TRUP TRUPANION, INC. | MOption exercise Common Stock | +313 | - | - | 35,036 | Feb 24, 2026 |
| Feb 22, 2026 | TRUP TRUPANION, INC. | MOption exercise Common Stock | +6,250 | - | - | 41,286 | Feb 24, 2026 |
| Feb 22, 2026 | TRUP TRUPANION, INC. | MOption exercise Restricted Stock Unit (RSU)derivative | -313 | $0.00 | $0 | 2,500 | Feb 24, 2026 |
| Feb 22, 2026 | TRUP TRUPANION, INC. | MOption exercise Restricted Stock Unit (RSU)derivative | -6,250 | $0.00 | $0 | 0 | Feb 24, 2026 |
| Nov 25, 2025 | TRUP TRUPANION, INC. | MOption exercise Common Stock | +946 | - | - | 34,723 | Nov 26, 2025 |
| Nov 25, 2025 | TRUP TRUPANION, INC. | MOption exercise Restricted Stock Unit (RSU)derivative | -946 | $0.00 | $0 | 946 | Nov 26, 2025 |
| Nov 24, 2025 | TRUP TRUPANION, INC. | MOption exercise Common Stock | +312 | - | - | 27,527 | Nov 25, 2025 |
| Nov 24, 2025 | TRUP TRUPANION, INC. | MOption exercise Common Stock | +6,250 | - | - | 33,777 | Nov 25, 2025 |
| Nov 24, 2025 | TRUP TRUPANION, INC. | MOption exercise Restricted Stock Unit (RSU)derivative | -312 | $0.00 | $0 | 2,813 | Nov 25, 2025 |
| Nov 24, 2025 | TRUP TRUPANION, INC. | MOption exercise Restricted Stock Unit (RSU)derivative | -6,250 | $0.00 | $0 | 6,250 | Nov 25, 2025 |
| Nov 20, 2025 | TRUP TRUPANION, INC. | MOption exercise Common Stock | +2,000 | $14.95 | $30k | 27,215 | Nov 20, 2025 |
| Nov 20, 2025 | TRUP TRUPANION, INC. | MOption exercise Stock Option (right to buy)derivative | -2,000 | $0.00 | $0 | 0 | Nov 20, 2025 |
| Sep 3, 2025 | TRUP TRUPANION, INC. | SOpen-market sale Common Stockindirect: By Kuyashii Primary Equities LLC | -19,631 | $44.79 | $879k | 1,443,650 | Sep 5, 2025 |
| Sep 4, 2025 | TRUP TRUPANION, INC. | SOpen-market sale Common Stockindirect: By Kuyashii Primary Equities LLC | -30,369 | $44.70 | $1.4M | 1,413,281 | Sep 5, 2025 |
| May 22, 2025 | TRUP TRUPANION, INC. | MOption exercise Common Stock | +6,250 | - | - | 650,621 | Aug 27, 2025 |
| May 22, 2025 | TRUP TRUPANION, INC. | MOption exercise Common Stock | +312 | - | - | 650,933 | Aug 27, 2025 |
| May 22, 2025 | TRUP TRUPANION, INC. | MOption exercise Common Stock | +945 | - | - | 651,878 | Aug 27, 2025 |
| Aug 22, 2025 | TRUP TRUPANION, INC. | MOption exercise Common Stock | +6,250 | - | - | 23,956 | Aug 27, 2025 |
| Aug 22, 2025 | TRUP TRUPANION, INC. | MOption exercise Common Stock | +313 | - | - | 24,269 | Aug 27, 2025 |
| Aug 25, 2025 | TRUP TRUPANION, INC. | MOption exercise Common Stock | +946 | - | - | 25,215 | Aug 27, 2025 |
| May 22, 2025 | TRUP TRUPANION, INC. | MOption exercise Restricted Stock Unit (RSU)derivative | -6,250 | $0.00 | $0 | 18,750 | Aug 27, 2025 |
| May 22, 2025 | TRUP TRUPANION, INC. | MOption exercise Restricted Stock Unit (RSU)derivative | -312 | $0.00 | $0 | 3,438 | Aug 27, 2025 |
| May 22, 2025 | TRUP TRUPANION, INC. | MOption exercise Restricted Stock Unit (RSU)derivative | -945 | $0.00 | $0 | 2,838 | Aug 27, 2025 |
| Aug 22, 2025 | TRUP TRUPANION, INC. | MOption exercise Restricted Stock Unit (RSU)derivative | -6,250 | $0.00 | $0 | 12,500 | Aug 27, 2025 |
| Aug 22, 2025 | TRUP TRUPANION, INC. | MOption exercise Restricted Stock Unit (RSU)derivative | -313 | $0.00 | $0 | 3,125 | Aug 27, 2025 |
| Aug 25, 2025 | TRUP TRUPANION, INC. | MOption exercise Restricted Stock Unit (RSU)derivative | -946 | $0.00 | $0 | 1,892 | Aug 27, 2025 |
| Nov 25, 2024 | TRUP TRUPANION, INC. | MOption exercise Common Stock | +946 | - | - | 630,819 | Nov 27, 2024 |
| Nov 25, 2024 | TRUP TRUPANION, INC. | FTax withholding Common Stock | -372 | $53.46 | $20k | 630,447 | Nov 27, 2024 |
| Nov 25, 2024 | TRUP TRUPANION, INC. | MOption exercise Common Stock | +2,738 | - | - | 633,185 | Nov 27, 2024 |
| Nov 25, 2024 | TRUP TRUPANION, INC. | FTax withholding Common Stock | -1,077 | $53.46 | $58k | 632,108 | Nov 27, 2024 |
| Nov 22, 2024 | TRUP TRUPANION, INC. | MOption exercise Common Stock | +6,250 | - | - | 638,358 | Nov 27, 2024 |
| Nov 22, 2024 | TRUP TRUPANION, INC. | FTax withholding Common Stock | -2,177 | $53.60 | $117k | 636,181 | Nov 27, 2024 |
| Nov 25, 2024 | TRUP TRUPANION, INC. | MOption exercise Restricted Stock Unit (RSU)derivative | -946 | $0.00 | $0 | 4,729 | Nov 27, 2024 |
| Nov 25, 2024 | TRUP TRUPANION, INC. | MOption exercise Restricted Stock Unit (RSU)derivative | -2,738 | $0.00 | $0 | 2,738 | Nov 27, 2024 |
| Nov 22, 2024 | TRUP TRUPANION, INC. | MOption exercise Restricted Stock Unit (RSU)derivative | -6,250 | $0.00 | $0 | 31,250 | Nov 27, 2024 |
| Feb 27, 2024 | TRUP TRUPANION, INC. | MOption exercise Common Stock | +803 | - | - | 594,330 | Feb 29, 2024 |
| Feb 27, 2024 | TRUP TRUPANION, INC. | FTax withholding Common Stock | -188 | $27.27 | $5,127 | 594,142 | Feb 29, 2024 |
| Feb 27, 2024 | TRUP TRUPANION, INC. | AGrant or award Restricted Stock Unit (RSU)derivative | +5,000 | $0.00 | $0 | 5,000 | Feb 29, 2024 |
| Feb 27, 2024 | TRUP TRUPANION, INC. | AGrant or award Restricted Stock Unit (RSU)derivative | +50,000 | $0.00 | $0 | 50,000 | Feb 29, 2024 |
| Feb 27, 2024 | TRUP TRUPANION, INC. | AGrant or award Restricted Stock Unit (RSU)derivative | +803 | $0.00 | $0 | 803 | Feb 29, 2024 |
| Feb 27, 2024 | TRUP TRUPANION, INC. | MOption exercise Restricted Stock Unit (RSU)derivative | -803 | $0.00 | $0 | 0 | Feb 29, 2024 |
| Feb 25, 2024 | TRUP TRUPANION, INC. | MOption exercise Common Stock | +2,098 | - | - | 591,556 | Feb 27, 2024 |
| Feb 25, 2024 | TRUP TRUPANION, INC. | FTax withholding Common Stock | -622 | $23.00 | $14k | 590,934 | Feb 27, 2024 |
Questions about Darryl Rawlings
Answered from the filings on this page, as of the latest one.
Is Darryl Rawlings buying or selling?
Not in the last 12 months. Darryl Rawlings's latest open-market trade on SEC Form 4 was sold $2.2M of TRUP on Sep 3, 2025.
How did Darryl Rawlings's past buys perform?
Not measured yet. InsiderTell needs three past buys with six months of prices to publish a track record, and Darryl Rawlings has 0.
Where does Darryl Rawlings file Form 4?
Darryl Rawlings has filed Form 4 at TRUP (TRUPANION, INC.) as Chief Executive Officer. A Form 4 is required of officers, directors and holders of more than 10% of a share class within two business days of a trade.
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.