X0508 4 2024-05-03 0001754226 Orange County Bancorp, Inc. /DE/ OBT 0001876359 Listner Michael 212 DOLSON AVENUE MIDDLETOWN NY 10940 1 SVP and CCO 0 Common Stock 2024-05-03 4 S 0 264 50 D 3781 D Includes shares of restricted stock which vest at a rate of 1/3 per year commencing on February 15, 2022. Includes restricted stock units which vest at a rate of 1/3 per year commencing on September 21, 2022. Includes restricted stock units which vest at a rate of 1/3 per year commencing on February 15, 2023. Includes restricted stock units which vest at a rate of 1/3 per year commencing on March 11, 2024 Includes restricted stock units which vest at a rate of 1/3 per year commencing on March 21, 2025 /s/ Jennifer Staub, pursuant to power of attorney 2024-05-07