| 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 | 550 | $36.14 | $19.9k | | 07/03/2023 |
| 06/15/2023 | Orange County Bancorp, Inc. /DE/ | OBT | Grant | Phantom Stock | 37 | $32.87 | $1.2k | | 06/15/2023 |
| 04/03/2023 | Orange County Bancorp, Inc. /DE/ | OBT | Grant | Phantom Stock | 451 | $43.99 | $19.8k | | 04/03/2023 |
| 03/15/2023 | Orange County Bancorp, Inc. /DE/ | OBT | Grant | Phantom Stock | 22 | $49.63 | $1.1k | | 03/15/2023 |
| 01/03/2023 | Orange County Bancorp, Inc. /DE/ | OBT | Grant | Phantom Stock | 424 | $46.85 | $19.9k | | 01/03/2023 |
| 12/15/2022 | Orange County Bancorp, Inc. /DE/ | OBT | Grant | Phantom Stock | 21 | $46.93 | $985.5 | | 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 | 472 | $39.49 | $18.6k | | 10/03/2022 |
| 09/15/2022 | Orange County Bancorp, Inc. /DE/ | OBT | Grant | Phantom Stock | 19 | $38.95 | $740 | | 09/15/2022 |
| 07/01/2022 | Orange County Bancorp, Inc. /DE/ | OBT | Grant | Phantom Stock | 491 | $37.99 | $18.7k | | 07/01/2022 |
| 06/15/2022 | Orange County Bancorp, Inc. /DE/ | OBT | Grant | Phantom Stock | 17.79 | $36.43 | $648.1 | | 06/15/2022 |
| 06/01/2022 | Orange County Bancorp, Inc. /DE/ | OBT | Grant | Phantom Stock | 167.529 | $37.11 | $6.2k | | 06/01/2022 |
| 05/02/2022 | Orange County Bancorp, Inc. /DE/ | OBT | Grant | Phantom Stock | 160.1494 | $38.82 | $6.2k | | 05/02/2022 |
| 04/01/2022 | Orange County Bancorp, Inc. /DE/ | OBT | Grant | Phantom Stock | 157.3725 | $39.51 | $6.2k | | 04/01/2022 |
| 03/15/2022 | Orange County Bancorp, Inc. /DE/ | OBT | Grant | Phantom Stock | 13.46 | $40.78 | $548.8 | | 03/15/2022 |
| 03/01/2022 | Orange County Bancorp, Inc. /DE/ | OBT | Grant | Phantom Stock | 151.8193 | $40.95 | $6.2k | | 03/01/2022 |
| 02/01/2022 | Orange County Bancorp, Inc. /DE/ | OBT | Grant | Phantom Stock | 151.6341 | $41.00 | $6.2k | | 02/01/2022 |
| 01/03/2022 | Orange County Bancorp, Inc. /DE/ | OBT | Grant | Phantom Stock | 152.5644 | $40.75 | $6.2k | | 01/03/2022 |
| 12/01/2021 | Orange County Bancorp, Inc. /DE/ | OBT | Grant | Phantom Stock | 177.3246 | $35.06 | $6.2k | | 12/01/2021 |
| 11/01/2021 | Orange County Bancorp, Inc. /DE/ | OBT | Grant | Phantom Stock | 167.3486 | $37.15 | $6.2k | | 11/01/2021 |
| 10/01/2021 | Orange County Bancorp, Inc. /DE/ | OBT | Grant | Phantom Stock | 175.2255 | $35.48 | $6.2k | | 10/01/2021 |
| 09/21/2021 | Orange County Bancorp, Inc. /DE/ | OBT | Grant | Common Stock | 2k | $0.00 | $0 | | 09/01/2021 |
| 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 | 177.6793 | $34.99 | $6.2k | | 09/01/2021 |
| 09/01/2021 | Orange County Bancorp, Inc. /DE/ | OBT | Grant | Phantom Stock | 167.59 | $34.99 | $5.9k | | 09/01/2021 |
| 08/05/2021 | Orange County Bancorp, Inc. /DE/ | OBT | Purchase | Common Stock | 11.5k | $33.50 | $385.2k | | 08/05/2021 |