| 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 | 104 | $36.14 | $3.8k | | 07/03/2023 |
| 06/15/2023 | Orange County Bancorp, Inc. /DE/ | OBT | Grant | Phantom Stock | 7 | $32.87 | $230.1 | | 06/15/2023 |
| 04/03/2023 | Orange County Bancorp, Inc. /DE/ | OBT | Grant | Phantom Stock | 85 | $43.99 | $3.7k | | 04/03/2023 |
| 03/15/2023 | Orange County Bancorp, Inc. /DE/ | OBT | Grant | Phantom Stock | 4 | $49.63 | $198.5 | | 03/15/2023 |
| 01/03/2023 | Orange County Bancorp, Inc. /DE/ | OBT | Grant | Phantom Stock | 80 | $46.85 | $3.7k | | 01/03/2023 |
| 12/15/2022 | Orange County Bancorp, Inc. /DE/ | OBT | Grant | Phantom Stock | 4 | $46.93 | $187.7 | | 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 | 95 | $39.49 | $3.8k | | 10/03/2022 |
| 09/15/2022 | Orange County Bancorp, Inc. /DE/ | OBT | Grant | Phantom Stock | 4 | $38.95 | $155.8 | | 09/15/2022 |
| 07/01/2022 | Orange County Bancorp, Inc. /DE/ | OBT | Grant | Phantom Stock | 99 | $37.99 | $3.8k | | 07/01/2022 |
| 07/01/2022 | Orange County Bancorp, Inc. /DE/ | OBT | Grant | Phantom Stock | 99 | $37.99 | $3.8k | | 07/01/2022 |
| 06/15/2022 | Orange County Bancorp, Inc. /DE/ | OBT | Grant | Phantom Stock | 3.34 | $36.43 | $121.7 | | 06/15/2022 |
| 06/01/2022 | Orange County Bancorp, Inc. /DE/ | OBT | Grant | Phantom Stock | 33.6836 | $37.11 | $1.2k | | 06/01/2022 |
| 05/02/2022 | Orange County Bancorp, Inc. /DE/ | OBT | Grant | Phantom Stock | 32.1999 | $38.82 | $1.3k | | 05/02/2022 |
| 04/01/2022 | Orange County Bancorp, Inc. /DE/ | OBT | Grant | Phantom Stock | 31.6416 | $39.51 | $1.3k | | 04/01/2022 |
| 03/15/2022 | Orange County Bancorp, Inc. /DE/ | OBT | Grant | Phantom Stock | 2.5 | $40.78 | $101.9 | | 03/15/2022 |
| 03/01/2022 | Orange County Bancorp, Inc. /DE/ | OBT | Grant | Phantom Stock | 30.525 | $40.95 | $1.2k | | 03/01/2022 |
| 02/01/2022 | Orange County Bancorp, Inc. /DE/ | OBT | Grant | Phantom Stock | 30.4878 | $41.00 | $1.2k | | 02/01/2022 |
| 01/03/2022 | Orange County Bancorp, Inc. /DE/ | OBT | Grant | Phantom Stock | 30.6748 | $40.75 | $1.2k | | 01/03/2022 |
| 12/01/2021 | Orange County Bancorp, Inc. /DE/ | OBT | Grant | Phantom Stock | 31.3748 | $35.06 | $1.1k | | 12/01/2021 |
| 11/01/2021 | Orange County Bancorp, Inc. /DE/ | OBT | Grant | Phantom Stock | 29.6097 | $37.15 | $1.1k | | 11/01/2021 |
| 10/01/2021 | Orange County Bancorp, Inc. /DE/ | OBT | Grant | Phantom Stock | 35.48 | $35.48 | $1.3k | | 10/01/2021 |
| 09/21/2021 | Orange County Bancorp, Inc. /DE/ | OBT | Grant | Common Stock | 2k | $0.00 | $0 | | 09/01/2021 |
| 09/01/2021 | Orange County Bancorp, Inc. /DE/ | OBT | Grant | Phantom Stock | 31.44 | $34.99 | $1.1k | | 09/01/2021 |
| 08/05/2021 | Orange County Bancorp, Inc. /DE/ | OBT | Purchase | Common Stock | 750 | $33.50 | $25.1k | | 08/05/2021 |