| Date | Name | Symbol | Type | Security | Shares | Price | Value | Ownership | Reported |
| 03/14/2023 | COMMUNITY BANK SYSTEM, INC. | CBU | Grant | Phantom Stock (Deferred Stock Units) | 1.2k | $0.00 | $0 | | 03/14/2023 |
| 12/01/2022 | COMMUNITY BANK SYSTEM, INC. | CBU | Exercise | Phantom Stock (Deferred Compensation) | 1.2k | $0.00 | $0 | | 12/01/2022 |
| 03/15/2022 | COMMUNITY BANK SYSTEM, INC. | CBU | Grant | Phantom Stock (Deferred Stock Units) | 644 | $0.00 | $0 | | 03/15/2022 |
| 12/01/2021 | COMMUNITY BANK SYSTEM, INC. | CBU | Exercise | Phantom Stock (Deferred Compensation) | 1.2k | $0.00 | $0 | | 12/01/2021 |
| 03/16/2021 | COMMUNITY BANK SYSTEM, INC. | CBU | Grant | Phantom Stock (Deferred Stock Units) | 569 | $0.00 | $0 | | 03/16/2021 |
| 12/18/2020 | COMMUNITY BANK SYSTEM, INC. | CBU | Exercise | Stock Option | 4.6k | $29.79 | $138k | | 12/18/2020 |
| 12/18/2020 | COMMUNITY BANK SYSTEM, INC. | CBU | Exercise | Stock Option | 2k | $28.78 | $57.6k | | 12/18/2020 |
| 12/18/2020 | COMMUNITY BANK SYSTEM, INC. | CBU | Sale | Common Stock | 6.6k | $64.15 | $425.4k | | 12/18/2020 |
| 12/01/2020 | COMMUNITY BANK SYSTEM, INC. | CBU | Exercise | Phantom Stock (Deferred Compensation) | 1.2k | $0.00 | $0 | | 12/01/2020 |
| 10/28/2020 | COMMUNITY BANK SYSTEM, INC. | CBU | Grant | Stock Option | 796 | $58.12 | $46.3k | | 10/28/2020 |
| 03/17/2020 | COMMUNITY BANK SYSTEM, INC. | CBU | Grant | Stock Option | 3.2k | $51.64 | $163.8k | | 03/17/2020 |
| 03/20/2019 | COMMUNITY BANK SYSTEM, INC. | CBU | Grant | Stock Option | 2.4k | $59.41 | $141.9k | | 03/20/2019 |
| 08/21/2018 | COMMUNITY BANK SYSTEM, INC. | CBU | Exercise | Stock Option | 2.6k | $28.78 | $73.8k | | 08/21/2018 |
| 08/21/2018 | COMMUNITY BANK SYSTEM, INC. | CBU | Sale | Common Stock | 2.6k | $66.27 | $170.1k | | 08/21/2018 |
| 03/20/2018 | COMMUNITY BANK SYSTEM, INC. | CBU | Grant | Stock Option | 2.6k | $55.92 | $143.1k | | 03/20/2018 |
| 02/16/2017 | COMMUNITY BANK SYSTEM, INC. | CBU | Sale | Common Stock | 3.8k | $59.97 | $230.9k | | 02/16/2017 |
| 02/16/2017 | COMMUNITY BANK SYSTEM, INC. | CBU | Exercise | Stock Option | 3.8k | $27.36 | $105.3k | | 02/16/2017 |
| 09/27/2012 | COMMUNITY BANK SYSTEM, INC. | CBU | Grant | Phantom Stock (Deferred Compensation) | 419.2872 | $28.62 | $12k | | 09/27/2012 |
| 07/20/2012 | COMMUNITY BANK SYSTEM, INC. | CBU | Grant | Phantom Stock (Deferred Compensation) | 130.1599 | $26.89 | $3.5k | | 07/20/2012 |
| 09/26/2011 | COMMUNITY BANK SYSTEM, INC. | CBU | Grant | Phantom Stock (Deferred Compensation) | 557.7006 | $23.31 | $13k | | 09/26/2011 |
| 03/22/2011 | COMMUNITY BANK SYSTEM, INC. | CBU | Grant | Phantom Stock (Deferred Compensation) | 487.9568 | $24.08 | $11.7k | | 03/22/2011 |
| 01/19/2011 | COMMUNITY BANK SYSTEM, INC. | CBU | Grant | Phantom Stock (Deferred Compensation) | 127.924 | $27.36 | $3.5k | | 01/19/2011 |
| 01/19/2011 | COMMUNITY BANK SYSTEM, INC. | CBU | Grant | Stock Option | 3.8k | $27.36 | $105.3k | | 01/19/2011 |
| 10/25/2010 | COMMUNITY BANK SYSTEM, INC. | CBU | Grant | Phantom Stock (Deferred Compensation) | 150.6672 | $23.23 | $3.5k | | 10/25/2010 |
| 06/25/2010 | COMMUNITY BANK SYSTEM, INC. | CBU | Grant | Phantom Stock (Deferred Compensation) | 269.5127 | $23.19 | $6.2k | | 06/25/2010 |