Orange County Bancorp, Inc. filed a Current Report on Form 8-K reporting that, on October 10, 2025, it delivered a notice to its directors and executive officers describing limitations on trading the company’s common stock. The notice concerns restrictions that apply to insiders and is provided as an exhibit to the filing. The company’s common stock trades under the ticker OBT and has a par value of $0.25. The filing is signed by the company’s Chief Financial Officer.
Olga Luz Tirado, a director of Orange County Bancorp, Inc. (OBT), reported transactions dated 10/01/2025. The filing shows a disposition of 2,097 shares of common stock and the acquisition of 50 phantom stock units that are the economic equivalent of common shares and become payable upon her separation as a director. The filing also notes restricted stock units that vest 100% on February 20, 2026 and will be settled in shares upon separation from service. Following the reported transactions the form lists 197 shares of common stock beneficially owned (direct). The form was signed under power of attorney on 10/02/2025.
Orange County Bancorp, Inc. (OBT) director Gregory F. Holcombe reported a set of equity transactions dated 10/01/2025. The filing shows a disposition of 68,953 shares of common stock. It also reports indirect holdings through entities: 14,920 shares held by a foundation, 69,440 shares held by an LLC, and 12,054 shares held in trust. The report lists phantom stock totaling 872 units (each unit economically equivalent to one common share) and restricted stock units (RSUs) that include one grant vesting fully on grant and another vesting on February 20, 2026. The phantom units and RSUs are payable or settled in common shares upon the reporting person’s separation from service.
Kevin J. Keane, a director of Orange County Bancorp, Inc. (OBT), reported changes in his beneficial ownership on Form 4. On 10/01/2025 Mr. Keane disposed of 19,395 shares of common stock (transaction code V). The filing shows he continues to have indirect holdings of 7,400 shares through a partnership and 832 shares through a 401(k). The report also shows the acquisition on 10/01/2025 of 769 units of phantom stock (each economically equivalent to one common share), which become payable upon his separation from service, and 15,565 shares beneficially owned following the derivative transaction. The filing discloses restricted stock units: some vesting 100% as of the grant date and others vesting 100% on February 20, 2026, and were to be settled in common shares upon separation. The Form 4 was signed under power of attorney on 10/02/2025.
Orange County Bancorp insider filing (Form 4) — Jonathan F. Rouis, a company director, reported transactions dated 10/01/2025. The filing shows a disposition of 9,295 shares of common stock and continued indirect ownership of 400 shares through his spouse. The filing also records a grant/acquisition of 179 units of phantom stock priced at $25.10 per share equivalent, which are payable upon the reporting person’s separation as a director. Following the reported derivative activity, the reporting person beneficially owns 5,837 shares attributable to derivative securities. The form is signed via power of attorney on 10/02/2025.
Richard B. Rowley, a director of Orange County Bancorp, Inc. (OBT), reported transactions dated 10/01/2025. The filing shows a disposition of 537,263 shares of common stock. The report also shows acquisition entries for 872 phantom stock units (each unit equals one share and becomes payable upon separation of service) and lists 22,563 common shares as beneficially owned following reported derivative holdings. The filing explains that certain restricted stock units (RSUs) vest 100% as of the grant date and others vest 100% on February 20, 2026, and RSUs are settled in issuer common stock upon separation from service.
Jon Schiller, a director of Orange County Bancorp, Inc. (OBT), reported transactions dated 10/01/2025. The filing shows 12,446 shares of common stock disposed and records the acquisition of 769 units of phantom stock that are the economic equivalent of one share each and become payable upon his separation as a director. The form also notes restricted stock units that vest 100% on February 20, 2026 and are settled in shares of the issuer's common stock upon the reporting person’s separation from service.
The Form 4 was signed on behalf of the reporting person by Jennifer Staub under power of attorney on 10/02/2025. The filing identifies Schiller’s relationship to the issuer as a director and is a single-person Form 4 submission.
Orange County Bancorp, Inc. filed a Form D announcing a completed exempt offering under Rule 506(b) for debt securities totaling $25,000,000. The issuer is a Delaware corporation with principal offices in Middletown, New York. The offering sold the full amount with 21 investors and a minimum outside investment of $100,000. Piper Sandler & Co. acted as (associated) broker-dealer. Reported sales commissions were $375,000. The company stated $0 of proceeds were used to pay named officers, directors or promoters. The notice was signed by EVP & CFO Michael Lesler.
Orange County Bancorp, Inc. disclosed entry into a material definitive agreement and the creation of a direct financial obligation related to a new subordinated note offering. The exhibits include the form of a 6.50% Fixed-to-Floating Rate Subordinated Note due 2035, a Subordinated Note Purchase Agreement form and an investor presentation. No financial statements or pro forma schedules were provided and no shell company transactions are reported. The filing lists the company contact and the CFO as the signing executive.
William D. Morrison, a director of Orange County Bancorp, Inc. (OBT), reported transactions dated 09/16/2025. The filing shows 102,639 shares of common stock listed as disposed (noted with footnotes regarding restricted stock units), ownership of 10,932 shares held in an IRA and 324 shares held in a Roth IRA following the reported transactions, and a grant/entry for phantom stock tied to 6 underlying common shares. Explanatory notes state some amounts represent restricted stock units that vest either immediately or on February 20, 2026 and that phantom stock is payable upon separation of service. The Form 4 is signed by a power of attorney on 09/17/2025.