| 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 | | 03/13/2023 |
| 03/13/2023 | COMMUNITY BANK SYSTEM, INC. | CBU | Sale | Common Stock | 483 | $52.57 | $25.4k | | 03/13/2023 |
| 03/13/2023 | COMMUNITY BANK SYSTEM, INC. | CBU | Exercise | Stock Option | 483 | $29.79 | $14.4k | | 03/13/2023 |
| 01/03/2023 | COMMUNITY BANK SYSTEM, INC. | CBU | Exercise | Phantom Stock (Deferred Compensation) | 3.4k | $0.00 | $0 | | 01/03/2023 |
| 03/15/2022 | COMMUNITY BANK SYSTEM, INC. | CBU | Grant | Phantom Stock (Deferred Stock Units) | 644 | $0.00 | $0 | | 03/15/2022 |
| 01/03/2022 | COMMUNITY BANK SYSTEM, INC. | CBU | Exercise | Phantom Stock (Deferred Compensation) | 3.3k | $0.00 | $0 | | 01/03/2022 |
| 03/16/2021 | COMMUNITY BANK SYSTEM, INC. | CBU | Grant | Phantom Stock (Deferred Stock Units) | 569 | $0.00 | $0 | | 03/16/2021 |
| 02/12/2021 | COMMUNITY BANK SYSTEM, INC. | CBU | Exercise | Stock Option | 4.6k | $28.78 | $131.4k | | 02/12/2021 |
| 02/12/2021 | COMMUNITY BANK SYSTEM, INC. | CBU | Sale | Common Stock | 4.6k | $69.91 | $319.2k | | 02/12/2021 |
| 11/09/2020 | COMMUNITY BANK SYSTEM, INC. | CBU | Exercise | Stock Option | 3.8k | $27.36 | $105.3k | | 11/09/2020 |
| 11/09/2020 | COMMUNITY BANK SYSTEM, INC. | CBU | Sale | Common Stock | 3.8k | $65.96 | $253.9k | | 11/09/2020 |
| 10/28/2020 | COMMUNITY BANK SYSTEM, INC. | CBU | Grant | Phantom Stock (Deferred Stock Units) | 172 | $0.00 | $0 | | 10/28/2020 |
| 03/17/2020 | COMMUNITY BANK SYSTEM, INC. | CBU | Grant | Phantom Stock (Deferred Stock Units) | 667 | $0.00 | $0 | | 03/17/2020 |
| 01/02/2020 | COMMUNITY BANK SYSTEM, INC. | CBU | Exercise | Phantom Stock (Deferred Compensation) | 3.1k | $0.00 | $0 | | 01/02/2020 |
| 09/19/2019 | COMMUNITY BANK SYSTEM, INC. | CBU | Gift | Common Stock | 390 | $0.00 | $0 | | 09/19/2019 |
| 06/28/2019 | COMMUNITY BANK SYSTEM, INC. | CBU | Sale | Common Stock | 4.5k | $65.78 | $294.1k | | 06/28/2019 |
| 06/28/2019 | COMMUNITY BANK SYSTEM, INC. | CBU | Exercise | Stock Option | 4.5k | $19.48 | $87.1k | | 06/28/2019 |
| 03/20/2019 | COMMUNITY BANK SYSTEM, INC. | CBU | Grant | Phantom Stock (Deferred Stock Units) | 576 | $0.00 | $0 | | 03/20/2019 |
| 01/02/2019 | COMMUNITY BANK SYSTEM, INC. | CBU | Exercise | Phantom Stock (Deferred Compensation) | 3k | $0.00 | $0 | | 01/02/2019 |
| 05/17/2018 | COMMUNITY BANK SYSTEM, INC. | CBU | Sale | Common Stock | 4.8k | $60.70 | $292.7k | | 05/17/2018 |
| 05/17/2018 | COMMUNITY BANK SYSTEM, INC. | CBU | Exercise | Stock Option | 4.8k | $18.08 | $87.2k | | 05/17/2018 |
| 03/20/2018 | COMMUNITY BANK SYSTEM, INC. | CBU | Grant | Phantom Stock (Deferred Stock Units) | 611 | $0.00 | $0 | | 03/20/2018 |
| 01/02/2017 | COMMUNITY BANK SYSTEM, INC. | CBU | Exercise | Phantom Stock (Deferred Compensation) | 3k | $0.00 | $0 | | 01/02/2017 |
| 08/29/2013 | COMMUNITY BANK SYSTEM, INC. | CBU | Grant | Phantom Stock (Deferred Compensation) | 2.2k | $33.85 | $76.2k | | 08/29/2013 |
| 08/29/2013 | COMMUNITY BANK SYSTEM, INC. | CBU | Grant | Phantom Stock (Deferred Compensation) | 66.4697 | $33.85 | $2.2k | | 08/29/2013 |
| 11/26/2012 | COMMUNITY BANK SYSTEM, INC. | CBU | Grant | Phantom Stock (Deferred Compensation) | 36.9413 | $27.07 | $1k | | 11/26/2012 |
| 09/27/2012 | COMMUNITY BANK SYSTEM, INC. | CBU | Grant | Phantom Stock (Deferred Compensation) | 419.2872 | $28.62 | $12k | | 09/27/2012 |
| 09/26/2011 | COMMUNITY BANK SYSTEM, INC. | CBU | Grant | Phantom Stock (Deferred Compensation) | 568.4256 | $23.31 | $13.3k | | 09/26/2011 |
| 08/18/2011 | COMMUNITY BANK SYSTEM, INC. | CBU | Purchase | Common Stock | 1000 | $22.37 | $22.4k | | 08/18/2011 |
| 06/27/2011 | COMMUNITY BANK SYSTEM, INC. | CBU | Grant | Phantom Stock (Deferred Compensation) | 346.6558 | $24.52 | $8.5k | | 06/27/2011 |
| 05/27/2011 | COMMUNITY BANK SYSTEM, INC. | CBU | Grant | Phantom Stock (Deferred Compensation) | 141.9878 | $24.65 | $3.5k | | 05/27/2011 |
| 02/24/2010 | COMMUNITY BANK SYSTEM, INC. | CBU | Sale | Common Stock | 2.4k | $22.40 | $54.4k | | 02/24/2010 |
| 12/16/2009 | COMMUNITY BANK SYSTEM, INC. | CBU | Grant | Phantom Stock (Deferred Compensation) | 522.508 | $18.66 | $9.7k | | 12/16/2009 |
| 11/27/2009 | COMMUNITY BANK SYSTEM, INC. | CBU | Grant | Phantom Stock (Deferred Compensation) | 111.1111 | $18.00 | $2k | | 11/27/2009 |