Darryl Rawlings, a director at Trupanion, Inc. ($TRUP), made two open market sales of common shares in the last 365 days, totaling about $2.24 million. His most recent sale occurred on September 4, 2025. These sales rank 3,276th among 11,678 individual insiders in our database, where the average is roughly $8.6 million across about 6.4 transactions. Rawlings had no open market purchases during this period.
| Transaction Date | Company | Ticker | Insider Name | Title | Transaction Type | Security | Shares | Price | Shares Owned Following | Total Shares Outstanding | % of Owned | % of Outstanding |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Feb. 25, 2026 | TRUPANION, INC. | $TRUP | RAWLINGS DARRYL | Director | M | Common Stock | 946 | $0.00 | 42,232.0000 | 43,555,884 | 2.29% | 0.00% |
| Feb. 25, 2026 | TRUPANION, INC. | $TRUP | RAWLINGS DARRYL | Director | M | Restricted Stock Unit (RSU) | 946 | $0.00 | 0.0000 | 43,555,884 | 100.00% | 0.00% |
| Feb. 22, 2026 | TRUPANION, INC. | $TRUP | RAWLINGS DARRYL | Director | M | Common Stock | 6250 | $0.00 | 41,286.0000 | 43,555,884 | 17.84% | 0.01% |
| Feb. 22, 2026 | TRUPANION, INC. | $TRUP | RAWLINGS DARRYL | Director | M | Common Stock | 313 | $0.00 | 35,036.0000 | 43,555,884 | 0.90% | 0.00% |
| Feb. 22, 2026 | TRUPANION, INC. | $TRUP | RAWLINGS DARRYL | Director | M | Restricted Stock Unit (RSU) | 6250 | $0.00 | 0.0000 | 43,555,884 | 100.00% | 0.01% |
| Feb. 22, 2026 | TRUPANION, INC. | $TRUP | RAWLINGS DARRYL | Director | M | Restricted Stock Unit (RSU) | 313 | $0.00 | 2,500.0000 | 43,555,884 | 11.13% | 0.00% |
| Nov. 25, 2025 | TRUPANION, INC. | $TRUP | RAWLINGS DARRYL | Director | M | Common Stock | 946 | $0.00 | 34,723.0000 | 43,562,132 | 2.80% | 0.00% |
| Nov. 25, 2025 | TRUPANION, INC. | $TRUP | RAWLINGS DARRYL | Director | M | Restricted Stock Unit (RSU) | 946 | $0.00 | 946.0000 | 43,562,132 | 50.00% | 0.00% |
| Nov. 24, 2025 | TRUPANION, INC. | $TRUP | RAWLINGS DARRYL | Director | M | Common Stock | 312 | $0.00 | 27,527.0000 | 43,562,132 | 1.15% | 0.00% |
| Nov. 24, 2025 | TRUPANION, INC. | $TRUP | RAWLINGS DARRYL | Director | M | Common Stock | 6250 | $0.00 | 33,777.0000 | 43,562,132 | 22.70% | 0.01% |
| Nov. 24, 2025 | TRUPANION, INC. | $TRUP | RAWLINGS DARRYL | Director | M | Restricted Stock Unit (RSU) | 312 | $0.00 | 2,813.0000 | 43,562,132 | 9.98% | 0.00% |
| Nov. 24, 2025 | TRUPANION, INC. | $TRUP | RAWLINGS DARRYL | Director | M | Restricted Stock Unit (RSU) | 6250 | $0.00 | 6,250.0000 | 43,562,132 | 50.00% | 0.01% |
| Nov. 20, 2025 | TRUPANION, INC. | $TRUP | RAWLINGS DARRYL | Director | M | Common Stock | 2000 | $14.95 | 27,215.0000 | 43,562,132 | 7.93% | 0.00% |
| Nov. 20, 2025 | TRUPANION, INC. | $TRUP | RAWLINGS DARRYL | Director | M | Stock Option (right to buy) | 2000 | $0.00 | 0.0000 | 43,562,132 | 100.00% | 0.00% |
| Sept. 4, 2025 | TRUPANION, INC. | $TRUP | RAWLINGS DARRYL | Director | S | Common Stock | 30369 | $44.70 | 1,413,281.0000 | 42,158,773 | 2.10% | 0.07% |
| Sept. 3, 2025 | TRUPANION, INC. | $TRUP | RAWLINGS DARRYL | Director | S | Common Stock | 19631 | $44.79 | 1,443,650.0000 | 42,158,773 | 1.34% | 0.05% |
| Aug. 22, 2025 | TRUPANION, INC. | $TRUP | RAWLINGS DARRYL | Director | M | Common Stock | 313 | $0.00 | 1,487,550.0000 | 42,158,773 | 0.02% | 0.00% |
| May 22, 2025 | TRUPANION, INC. | $TRUP | RAWLINGS DARRYL | Director | M | Common Stock | 945 | $0.00 | 2,115,159.0000 | 42,158,773 | 0.04% | 0.00% |
| May 22, 2025 | TRUPANION, INC. | $TRUP | RAWLINGS DARRYL | Director | M | Common Stock | 312 | $0.00 | 2,114,214.0000 | 42,158,773 | 0.01% | 0.00% |
| May 22, 2025 | TRUPANION, INC. | $TRUP | RAWLINGS DARRYL | Director | M | Common Stock | 6250 | $0.00 | 2,113,902.0000 | 42,158,773 | 0.30% | 0.01% |
| Aug. 22, 2025 | TRUPANION, INC. | $TRUP | RAWLINGS DARRYL | Director | M | Restricted Stock Unit (RSU) | 6250 | $0.00 | 12,500.0000 | 42,158,773 | 33.33% | 0.01% |
| May 22, 2025 | TRUPANION, INC. | $TRUP | RAWLINGS DARRYL | Director | M | Restricted Stock Unit (RSU) | 945 | $0.00 | 2,838.0000 | 42,158,773 | 24.98% | 0.00% |
| May 22, 2025 | TRUPANION, INC. | $TRUP | RAWLINGS DARRYL | Director | M | Restricted Stock Unit (RSU) | 312 | $0.00 | 3,438.0000 | 42,158,773 | 8.32% | 0.00% |
| May 22, 2025 | TRUPANION, INC. | $TRUP | RAWLINGS DARRYL | Director | M | Restricted Stock Unit (RSU) | 6250 | $0.00 | 18,750.0000 | 42,158,773 | 25.00% | 0.01% |
| Aug. 25, 2025 | TRUPANION, INC. | $TRUP | RAWLINGS DARRYL | Director | M | Common Stock | 946 | $0.00 | 1,488,496.0000 | 42,158,773 | 0.06% | 0.00% |
| Aug. 22, 2025 | TRUPANION, INC. | $TRUP | RAWLINGS DARRYL | Director | M | Common Stock | 6250 | $0.00 | 1,487,237.0000 | 42,158,773 | 0.42% | 0.01% |
| Aug. 25, 2025 | TRUPANION, INC. | $TRUP | RAWLINGS DARRYL | Director | M | Restricted Stock Unit (RSU) | 946 | $0.00 | 1,892.0000 | 42,158,773 | 33.33% | 0.00% |
| Aug. 22, 2025 | TRUPANION, INC. | $TRUP | RAWLINGS DARRYL | Director | M | Restricted Stock Unit (RSU) | 313 | $0.00 | 3,125.0000 | 42,158,773 | 9.10% | 0.00% |
| Feb. 25, 2025 | TRUPANION, INC. | $TRUP | RAWLINGS DARRYL | Director | M | Restricted Stock Unit (RSU) | 946 | $0.00 | 3,783.0000 | 42,158,773 | 20.00% | 0.00% |
| Feb. 25, 2025 | TRUPANION, INC. | $TRUP | RAWLINGS DARRYL | Director | M | Common Stock | 2738 | $0.00 | 644,321.0000 | 42,158,773 | 0.43% | 0.01% |
| Feb. 25, 2025 | TRUPANION, INC. | $TRUP | RAWLINGS DARRYL | Director | M | Restricted Stock Unit (RSU) | 2738 | $0.00 | 0.0000 | 42,158,773 | 100.00% | 0.01% |
| Feb. 25, 2025 | TRUPANION, INC. | $TRUP | RAWLINGS DARRYL | Director | F | Common Stock | 230 | $34.12 | 644,371.0000 | 42,158,773 | 0.04% | 0.00% |
| Feb. 25, 2025 | TRUPANION, INC. | $TRUP | RAWLINGS DARRYL | Director | M | Common Stock | 946 | $0.00 | 644,601.0000 | 42,158,773 | 0.15% | 0.00% |
| Feb. 25, 2025 | TRUPANION, INC. | $TRUP | RAWLINGS DARRYL | Director | F | Common Stock | 666 | $34.12 | 643,655.0000 | 42,158,773 | 0.10% | 0.00% |
| Feb. 24, 2025 | TRUPANION, INC. | $TRUP | RAWLINGS DARRYL | Director | M | Restricted Stock Unit (RSU) | 6250 | $0.00 | 25,000.0000 | 42,158,773 | 20.00% | 0.01% |
| Feb. 24, 2025 | TRUPANION, INC. | $TRUP | RAWLINGS DARRYL | Director | M | Common Stock | 6250 | $0.00 | 642,431.0000 | 42,158,773 | 0.98% | 0.01% |
| Feb. 24, 2025 | TRUPANION, INC. | $TRUP | RAWLINGS DARRYL | Director | F | Common Stock | 1728 | $33.41 | 640,703.0000 | 42,158,773 | 0.27% | 0.00% |
| Feb. 24, 2025 | TRUPANION, INC. | $TRUP | RAWLINGS DARRYL | Director | M | Common Stock | 1250 | $0.00 | 641,953.0000 | 42,158,773 | 0.20% | 0.00% |
| Feb. 24, 2025 | TRUPANION, INC. | $TRUP | RAWLINGS DARRYL | Director | F | Common Stock | 370 | $33.41 | 641,583.0000 | 42,158,773 | 0.06% | 0.00% |
| Feb. 24, 2025 | TRUPANION, INC. | $TRUP | RAWLINGS DARRYL | Director | M | Restricted Stock Unit (RSU) | 1250 | $0.00 | 3,750.0000 | 42,158,773 | 25.00% | 0.00% |
| Nov. 22, 2024 | TRUPANION, INC. | $TRUP | RAWLINGS DARRYL | Director | M | Restricted Stock Unit (RSU) | 6250 | $0.00 | 31,250.0000 | 42,822,505 | 16.67% | 0.01% |
| Nov. 25, 2024 | TRUPANION, INC. | $TRUP | RAWLINGS DARRYL | Director | M | Common Stock | 946 | $0.00 | 630,819.0000 | 42,822,505 | 0.15% | 0.00% |
| Nov. 25, 2024 | TRUPANION, INC. | $TRUP | RAWLINGS DARRYL | Director | F | Common Stock | 372 | $53.46 | 630,447.0000 | 42,822,505 | 0.06% | 0.00% |
| Nov. 25, 2024 | TRUPANION, INC. | $TRUP | RAWLINGS DARRYL | Director | M | Common Stock | 2738 | $0.00 | 633,185.0000 | 42,822,505 | 0.43% | 0.01% |
| Nov. 25, 2024 | TRUPANION, INC. | $TRUP | RAWLINGS DARRYL | Director | F | Common Stock | 1077 | $53.46 | 632,108.0000 | 42,822,505 | 0.17% | 0.00% |
| Nov. 22, 2024 | TRUPANION, INC. | $TRUP | RAWLINGS DARRYL | Director | M | Common Stock | 6250 | $0.00 | 638,358.0000 | 42,822,505 | 0.99% | 0.01% |
| Nov. 22, 2024 | TRUPANION, INC. | $TRUP | RAWLINGS DARRYL | Director | F | Common Stock | 2177 | $53.60 | 636,181.0000 | 42,822,505 | 0.34% | 0.01% |
| Nov. 25, 2024 | TRUPANION, INC. | $TRUP | RAWLINGS DARRYL | Director | M | Restricted Stock Unit (RSU) | 946 | $0.00 | 4,729.0000 | 42,822,505 | 16.67% | 0.00% |
| Nov. 25, 2024 | TRUPANION, INC. | $TRUP | RAWLINGS DARRYL | Director | M | Restricted Stock Unit (RSU) | 2738 | $0.00 | 2,738.0000 | 42,822,505 | 50.00% | 0.01% |
| Aug. 25, 2024 | TRUPANION, INC. | $TRUP | RAWLINGS DARRYL | Director | M | Restricted Stock Unit (RSU) | 946 | $0.00 | 5,675.0000 | 41,436,882 | 14.29% | 0.00% |
| Aug. 25, 2024 | TRUPANION, INC. | $TRUP | RAWLINGS DARRYL | Director | M | Common Stock | 946 | $0.00 | 628,031.0000 | 41,436,882 | 0.15% | 0.00% |
| Aug. 25, 2024 | TRUPANION, INC. | $TRUP | RAWLINGS DARRYL | Director | F | Common Stock | 230 | $46.63 | 627,801.0000 | 41,436,882 | 0.04% | 0.00% |
| Aug. 25, 2024 | TRUPANION, INC. | $TRUP | RAWLINGS DARRYL | Director | M | Common Stock | 2738 | $0.00 | 630,539.0000 | 41,436,882 | 0.44% | 0.01% |
| Aug. 25, 2024 | TRUPANION, INC. | $TRUP | RAWLINGS DARRYL | Director | F | Common Stock | 666 | $46.63 | 629,873.0000 | 41,436,882 | 0.11% | 0.00% |
| Aug. 25, 2024 | TRUPANION, INC. | $TRUP | RAWLINGS DARRYL | Director | M | Restricted Stock Unit (RSU) | 2738 | $0.00 | 5,476.0000 | 41,436,882 | 33.33% | 0.01% |
| Aug. 22, 2024 | TRUPANION, INC. | $TRUP | RAWLINGS DARRYL | Director | F | Common Stock | 1521 | $45.39 | 627,085.0000 | 41,436,882 | 0.24% | 0.00% |
| Aug. 22, 2024 | TRUPANION, INC. | $TRUP | RAWLINGS DARRYL | Director | M | Common Stock | 6250 | $0.00 | 628,606.0000 | 41,436,882 | 1.00% | 0.02% |
| Aug. 22, 2024 | TRUPANION, INC. | $TRUP | RAWLINGS DARRYL | Director | M | Restricted Stock Unit (RSU) | 6250 | $0.00 | 37,500.0000 | 41,436,882 | 14.29% | 0.02% |
| May 25, 2024 | TRUPANION, INC. | $TRUP | RAWLINGS DARRYL | Chief Executive Officer | M | Common Stock | 945 | $0.00 | 622,586.0000 | 41,436,882 | 0.15% | 0.00% |
| May 25, 2024 | TRUPANION, INC. | $TRUP | RAWLINGS DARRYL | Chief Executive Officer | M | Restricted Stock Unit (RSU) | 945 | $0.00 | 6,621.0000 | 41,436,882 | 12.49% | 0.00% |
| May 25, 2024 | TRUPANION, INC. | $TRUP | RAWLINGS DARRYL | Chief Executive Officer | M | Restricted Stock Unit (RSU) | 2737 | $0.00 | 8,214.0000 | 41,436,882 | 24.99% | 0.01% |
| May 25, 2024 | TRUPANION, INC. | $TRUP | RAWLINGS DARRYL | Chief Executive Officer | F | Common Stock | 230 | $28.95 | 622,356.0000 | 41,436,882 | 0.04% | 0.00% |
| May 25, 2024 | TRUPANION, INC. | $TRUP | RAWLINGS DARRYL | Chief Executive Officer | F | Common Stock | 666 | $28.95 | 621,641.0000 | 41,436,882 | 0.11% | 0.00% |
| May 25, 2024 | TRUPANION, INC. | $TRUP | RAWLINGS DARRYL | Chief Executive Officer | M | Common Stock | 2737 | $0.00 | 622,307.0000 | 41,436,882 | 0.44% | 0.01% |
| May 22, 2024 | TRUPANION, INC. | $TRUP | RAWLINGS DARRYL | Chief Executive Officer | M | Common Stock | 6250 | $0.00 | 621,092.0000 | 41,436,882 | 1.02% | 0.02% |
| May 22, 2024 | TRUPANION, INC. | $TRUP | RAWLINGS DARRYL | Chief Executive Officer | F | Common Stock | 1522 | $29.19 | 619,570.0000 | 41,436,882 | 0.25% | 0.00% |
| May 22, 2024 | TRUPANION, INC. | $TRUP | RAWLINGS DARRYL | Chief Executive Officer | M | Restricted Stock Unit (RSU) | 6250 | $0.00 | 43,750.0000 | 41,436,882 | 12.50% | 0.02% |
| May 7, 2024 | TRUPANION, INC. | $TRUP | RAWLINGS DARRYL | Chief Executive Officer | P | Common Stock | 20700 | $24.14 | 614,842.0000 | 41,436,882 | 3.48% | 0.05% |
| May 7, 2024 | TRUPANION, INC. | $TRUP | RAWLINGS DARRYL | Chief Executive Officer | P | Common Stock | 20700 | $24.14 | 614,842.0000 | 41,436,882 | 3.48% | 0.05% |
| Feb. 27, 2024 | TRUPANION, INC. | $TRUP | RAWLINGS DARRYL | Chief Executive Officer | F | Common Stock | 188 | $27.27 | 594,142.0000 | 41,436,882 | 0.03% | 0.00% |
| Feb. 27, 2024 | TRUPANION, INC. | $TRUP | RAWLINGS DARRYL | Chief Executive Officer | M | Restricted Stock Unit (RSU) | 803 | $0.00 | 0.0000 | 41,436,882 | 100.00% | 0.00% |
| Feb. 27, 2024 | TRUPANION, INC. | $TRUP | RAWLINGS DARRYL | Chief Executive Officer | A | Restricted Stock Unit (RSU) | 803 | $0.00 | 803.0000 | 41,436,882 | 9999.99% | 0.00% |
| Feb. 27, 2024 | TRUPANION, INC. | $TRUP | RAWLINGS DARRYL | Chief Executive Officer | A | Restricted Stock Unit (RSU) | 50000 | $0.00 | 50,000.0000 | 41,436,882 | 9999.99% | 0.12% |
| Feb. 27, 2024 | TRUPANION, INC. | $TRUP | RAWLINGS DARRYL | Chief Executive Officer | A | Restricted Stock Unit (RSU) | 5000 | $0.00 | 5,000.0000 | 41,436,882 | 9999.99% | 0.01% |
| Feb. 27, 2024 | TRUPANION, INC. | $TRUP | RAWLINGS DARRYL | Chief Executive Officer | M | Common Stock | 803 | $0.00 | 594,330.0000 | 41,436,882 | 0.14% | 0.00% |
| Feb. 25, 2024 | TRUPANION, INC. | $TRUP | RAWLINGS DARRYL | Chief Executive Officer | M | Common Stock | 2738 | $0.00 | 593,672.0000 | 41,436,882 | 0.46% | 0.01% |
| Feb. 25, 2024 | TRUPANION, INC. | $TRUP | RAWLINGS DARRYL | Chief Executive Officer | F | Common Stock | 622 | $23.00 | 590,934.0000 | 41,436,882 | 0.11% | 0.00% |
| Feb. 25, 2024 | TRUPANION, INC. | $TRUP | RAWLINGS DARRYL | Chief Executive Officer | M | Common Stock | 2098 | $0.00 | 591,556.0000 | 41,436,882 | 0.36% | 0.01% |
| Feb. 25, 2024 | TRUPANION, INC. | $TRUP | RAWLINGS DARRYL | Chief Executive Officer | M | Restricted Stock Unit (RSU) | 946 | $0.00 | 7,566.0000 | 41,436,882 | 11.11% | 0.00% |
| Feb. 25, 2024 | TRUPANION, INC. | $TRUP | RAWLINGS DARRYL | Chief Executive Officer | M | Restricted Stock Unit (RSU) | 2738 | $0.00 | 10,951.0000 | 41,436,882 | 20.00% | 0.01% |
| Feb. 25, 2024 | TRUPANION, INC. | $TRUP | RAWLINGS DARRYL | Chief Executive Officer | M | Restricted Stock Unit (RSU) | 2098 | $0.00 | 0.0000 | 41,436,882 | 100.00% | 0.01% |
| Feb. 25, 2024 | TRUPANION, INC. | $TRUP | RAWLINGS DARRYL | Chief Executive Officer | F | Common Stock | 280 | $23.00 | 593,527.0000 | 41,436,882 | 0.05% | 0.00% |
| Feb. 25, 2024 | TRUPANION, INC. | $TRUP | RAWLINGS DARRYL | Chief Executive Officer | M | Common Stock | 946 | $0.00 | 593,807.0000 | 41,436,882 | 0.16% | 0.00% |
| Feb. 25, 2024 | TRUPANION, INC. | $TRUP | RAWLINGS DARRYL | Chief Executive Officer | F | Common Stock | 811 | $23.00 | 592,861.0000 | 41,436,882 | 0.14% | 0.00% |