Darryl Rawlings serves as Executive at TRUPANION INC., where they oversee executive responsibilities. Since joining the company, Darryl Rawlings has executed 404 insider transactions totaling $48.4M, demonstrating a bearish approach to their equity position. Their most recent transaction on Nov 25, 2025 involved exercising options for 946 shares valued at $0.
Darryl Rawlings currently holds 34,723 shares of TRUPANION INC. (TRUP), valued at approximately $0. This represents their equity stake as Executive.
Based on SEC Form 4 filings, Darryl Rawlings has been a net seller of TRUP stock. They have purchased $999.4K and sold $47.4M worth of shares.
Darryl Rawlings's most recent insider trade was on Nov 25, 2025, when they sold 946 shares at $0.00 per share.
Get notified when new Form 4 filings are submitted
| $N/A |
| Discretionary |
| Nov 24, 2025 | TRUP | $0 | Option Exercise | 312 | $N/A | Discretionary |
| Nov 20, 2025 | TRUP | $29.9K | Option Exercise | 2,000 | $14.95 | Discretionary |
| Sep 4, 2025 | TRUP | $1.4M | Sale | 30,369 | $44.70 | Discretionary |
| Sep 3, 2025 | TRUP | $879.3K | Sale | 19,631 | $44.79 | Discretionary |
| Aug 25, 2025 | TRUP | $0 | Option Exercise | 946 | $N/A | Discretionary |
| Aug 22, 2025 | TRUP | $0 | Option Exercise | 6,250 | $N/A | Discretionary |
| Aug 22, 2025 | TRUP | $0 | Option Exercise | 313 | $N/A | Discretionary |
| May 22, 2025 | TRUP | $0 | Option Exercise | 6,250 | $N/A | Discretionary |
| May 22, 2025 | TRUP | $0 | Option Exercise | 312 | $N/A | Discretionary |
| May 22, 2025 | TRUP | $0 | Option Exercise | 945 | $N/A | Discretionary |
| Aug 25, 2024 | TRUP | $10.7K | Payment | 230 | $46.63 | Discretionary |
| Aug 25, 2024 | TRUP | $0 | Option Exercise | 2,738 | $N/A | Discretionary |
| Aug 25, 2024 | TRUP | $31.1K | Payment | 666 | $46.63 | Discretionary |
| Aug 25, 2024 | TRUP | $0 | Option Exercise | 946 | $N/A | Discretionary |
| Aug 22, 2024 | TRUP | $0 | Option Exercise | 6,250 | $N/A | Discretionary |
| Aug 22, 2024 | TRUP | $69.0K | Payment | 1,521 | $45.39 | Discretionary |
| May 25, 2024 | TRUP | $0 | Option Exercise | 945 | $N/A | Discretionary |
| May 25, 2024 | TRUP | $19.3K | Payment | 666 | $28.95 | Discretionary |
| May 25, 2024 | TRUP | $0 | Option Exercise | 2,737 | $N/A | Discretionary |
| May 25, 2024 | TRUP | $6.7K | Payment | 230 | $28.95 | Discretionary |
| May 22, 2024 | TRUP | $0 | Option Exercise | 6,250 | $N/A | Discretionary |
| May 22, 2024 | TRUP | $44.4K | Payment | 1,522 | $29.19 | Discretionary |
| May 7, 2024 | TRUP | $499.7K | Purchase | 20,700 | $24.14 | Discretionary |
| May 7, 2024 | TRUP | $499.7K | Purchase | 20,700 | $24.14 | Discretionary |
| Feb 27, 2024 | TRUP | $0 | Option Exercise | 803 | $N/A | Discretionary |
| Feb 27, 2024 | TRUP | $5.1K | Payment | 188 | $27.27 | Discretionary |
| Feb 25, 2024 | TRUP | $6.4K | Payment | 280 | $23.00 | Discretionary |
| Feb 25, 2024 | TRUP | $0 | Option Exercise | 946 | $N/A | Discretionary |