| Date | Name | Symbol | Type | Security | Shares | Price | Value | Ownership | Reported |
| 03/15/2023 | COMMUNITY BANK SYSTEM, INC. | CBU | Purchase | Common Stock | 2k | $53.20 | $106.4k | | 03/15/2023 |
| 03/15/2022 | COMMUNITY BANK SYSTEM, INC. | CBU | Exercise | Phantom Stock (Deferred Stock Units) | 578.8265 | $0.00 | $0 | | 03/15/2022 |
| 03/15/2022 | COMMUNITY BANK SYSTEM, INC. | CBU | Grant | Phantom Stock (Deferred Stock Units) | 644 | $0.00 | $0 | | 03/15/2022 |
| 03/16/2021 | COMMUNITY BANK SYSTEM, INC. | CBU | Grant | Phantom Stock (Deferred Stock Units) | 569 | $0.00 | $0 | | 03/16/2021 |
| 03/10/2021 | COMMUNITY BANK SYSTEM, INC. | CBU | Exercise | Stock Option | 3.6k | $37.77 | $137.1k | | 03/10/2021 |
| 03/10/2021 | COMMUNITY BANK SYSTEM, INC. | CBU | Exercise | Stock Option | 3.9k | $35.36 | $139.2k | | 03/10/2021 |
| 03/10/2021 | COMMUNITY BANK SYSTEM, INC. | CBU | Sale | Common Stock | 7.6k | $79.36 | $600.6k | | 03/10/2021 |
| 11/09/2020 | COMMUNITY BANK SYSTEM, INC. | CBU | Exercise | Stock Option | 4.6k | $29.79 | $138k | | 11/09/2020 |
| 11/09/2020 | COMMUNITY BANK SYSTEM, INC. | CBU | Exercise | Stock Option | 4.6k | $28.78 | $131.4k | | 11/09/2020 |
| 11/09/2020 | COMMUNITY BANK SYSTEM, INC. | CBU | Sale | Common Stock | 4.6k | $66.83 | $309.5k | | 11/09/2020 |
| 11/09/2020 | COMMUNITY BANK SYSTEM, INC. | CBU | Sale | Common Stock | 4.6k | $63.01 | $287.7k | | 11/09/2020 |
| 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 |
| 03/20/2018 | COMMUNITY BANK SYSTEM, INC. | CBU | Grant | Stock Option | 2.6k | $55.92 | $143.1k | | 03/20/2018 |
| 03/15/2017 | COMMUNITY BANK SYSTEM, INC. | CBU | Grant | Stock Option | 2.5k | $57.12 | $141.5k | | 03/15/2017 |
| 01/26/2017 | COMMUNITY BANK SYSTEM, INC. | CBU | Sale | Common Stock | 5k | $61.56 | $307.8k | By Charles E. Parente Revocable Trust | 01/26/2017 |
| 12/08/2016 | COMMUNITY BANK SYSTEM, INC. | CBU | Sale | Common Stock | 3.6k | $60.89 | $217.1k | By Charles E. Parente Revocable Trust | 12/08/2016 |
| 10/25/2013 | COMMUNITY BANK SYSTEM, INC. | CBU | Sale | Common Stock | 3.8k | $36.72 | $141.4k | | 10/25/2013 |
| 10/25/2013 | COMMUNITY BANK SYSTEM, INC. | CBU | Exercise | Stock Option | 3.8k | $27.36 | $105.3k | | 10/25/2013 |
| 07/26/2012 | COMMUNITY BANK SYSTEM, INC. | CBU | Gift | Common Stock | 1.2k | $0.00 | $0 | | 07/24/2012 |
| 07/24/2012 | COMMUNITY BANK SYSTEM, INC. | CBU | Gift | Common Stock | 4k | $0.00 | $0 | | 07/24/2012 |
| 04/10/2012 | COMMUNITY BANK SYSTEM, INC. | CBU | Other (acquisition) | Phantom Stock (Deferred Compensation) | 20.4313 | $27.66 | $565.1 | | 04/10/2012 |
| 08/02/2011 | COMMUNITY BANK SYSTEM, INC. | CBU | Purchase | Common Stock | 11k | $25.12 | $276.3k | | 08/02/2011 |
| 04/11/2011 | COMMUNITY BANK SYSTEM, INC. | CBU | Other (acquisition) | Phantom Stock (Deferred Compensation) | 20.3074 | $24.69 | $501.4 | | 04/11/2011 |
| 05/21/2010 | COMMUNITY BANK SYSTEM, INC. | CBU | Purchase | Common Stock | 2.6k | $21.80 | $56.7k | | 05/21/2010 |