Management Change/Compensation (Form 8-K)

(b) On July 21, 2025, Jeffrey M. Levy notified Community Financial System, Inc. (the "Company") of his intention to retire from his position as Senior Vice President ("SVP") and Chief Banking Officer of Community Bank, N.A. (the "Bank"), the Company's wholly owned subsidiary, effective as of December 31, 2025.

Mr. Levy has served as the Bank's SVP and Chief Banking Officer since January 1, 2024. Prior to his appointment as Chief Banking Officer, he served in several important roles in the Bank, including serving as the President, Commercial Banking, and the Regional President of Capital Region of New York. Mr. Levy has played an important part in Company's success over the last seven years, in particular with the growth of its commercial lending business and its expansion across the Capital Region. The Company extends its gratitude to him for his years of service and contributions to the Company and the Bank.

The Company has selected Matthew Durkee, the Bank's President, Commercial Banking, as Mr. Levy's successor. Mr. Durkee will assume his new role on January 1, 2026. Mr. Durkee joined the Bank in January 2022 as the Bank's President of the New England Region and was appointed as the President, Commercial Banking in January 2024, when Mr. Levy assumed the position of Chief Banking Officer.