X0306 4 2019-03-20 0000723188 COMMUNITY BANK SYSTEM, INC. CBU 0001485739 Whipple John F. C/O COMMUNITY BANK SYSTEM, INC. 5790 WIDEWATERS PARKWAY DEWITT NY 13214 1 Stock Option 59.41 2019-03-20 4 A 0 2388 0 A 2019-03-20 2029-03-20 Common Stock 2388 2388 D Phantom Stock (Deferred Compensation) Common Stock 11360.6893 11360.6893 D Each unit of phantom stock is the economic equivalent of one share of Community Bank System, Inc. common stock. The units of phantom stock relating to the Deferred Compensation Plan will be settled in Community Bank System, Inc. common stock at future dates selected by the reporting person. Includes 274.8281 units of phantom stock acquired under the Deferred Compensation Plan's dividend reinvestment feature. /s/ Danielle M. Cima, pursuant to a Confirming Statement executed by John F. Whipple, Jr. 2019-03-22