| Date | Name | Symbol | Type | Security | Shares | Price | Value | Ownership | Reported |
| 10/02/2023 | Orange County Bancorp, Inc. /DE/ | OBT | Grant | Phantom Stock | 0 | $42.50 | $0 | | 10/02/2023 |
| 08/08/2023 | Orange County Bancorp, Inc. /DE/ | OBT | Grant | Common Stock | 450 | $0.00 | $0 | | 08/08/2023 |
| 07/03/2023 | Orange County Bancorp, Inc. /DE/ | OBT | Grant | Phantom Stock | 498 | $36.14 | $18k | | 07/03/2023 |
| 06/15/2023 | Orange County Bancorp, Inc. /DE/ | OBT | Grant | Phantom Stock | 19 | $32.87 | $624.5 | | 06/15/2023 |
| 04/03/2023 | Orange County Bancorp, Inc. /DE/ | OBT | Grant | Phantom Stock | 409 | $43.99 | $18k | | 04/03/2023 |
| 03/15/2023 | Orange County Bancorp, Inc. /DE/ | OBT | Grant | Phantom Stock | 10 | $49.63 | $496.3 | | 03/15/2023 |
| 01/03/2023 | Orange County Bancorp, Inc. /DE/ | OBT | Grant | Phantom Stock | 384 | $46.85 | $18k | | 01/03/2023 |
| 12/15/2022 | Orange County Bancorp, Inc. /DE/ | OBT | Grant | Phantom Stock | 9 | $46.93 | $422.4 | | 12/15/2022 |
| 11/15/2022 | Orange County Bancorp, Inc. /DE/ | OBT | Grant | Common Stock | 300 | $0.00 | $0 | | 11/15/2022 |
| 10/03/2022 | Orange County Bancorp, Inc. /DE/ | OBT | Grant | Phantom Stock | 455 | $39.49 | $18k | | 10/03/2022 |
| 09/15/2022 | Orange County Bancorp, Inc. /DE/ | OBT | Grant | Phantom Stock | 7 | $38.95 | $272.6 | | 09/15/2022 |
| 07/01/2022 | Orange County Bancorp, Inc. /DE/ | OBT | Grant | Phantom Stock | 473 | $37.99 | $18k | | 07/01/2022 |
| 06/15/2022 | Orange County Bancorp, Inc. /DE/ | OBT | Grant | Phantom Stock | 4.99 | $36.43 | $181.8 | | 06/15/2022 |
| 06/01/2022 | Orange County Bancorp, Inc. /DE/ | OBT | Grant | Phantom Stock | 161.5467 | $37.11 | $6k | | 06/01/2022 |
| 05/02/2022 | Orange County Bancorp, Inc. /DE/ | OBT | Grant | Phantom Stock | 154.4307 | $38.82 | $6k | | 05/02/2022 |
| 04/01/2022 | Orange County Bancorp, Inc. /DE/ | OBT | Grant | Phantom Stock | 151.7529 | $39.51 | $6k | | 04/01/2022 |
| 03/15/2022 | Orange County Bancorp, Inc. /DE/ | OBT | Grant | Phantom Stock | 2.16 | $40.78 | $88.1 | | 03/15/2022 |
| 03/01/2022 | Orange County Bancorp, Inc. /DE/ | OBT | Grant | Phantom Stock | 146.398 | $40.95 | $6k | | 03/01/2022 |
| 02/01/2022 | Orange County Bancorp, Inc. /DE/ | OBT | Grant | Phantom Stock | 292.439 | $41.00 | $12k | | 02/01/2022 |