| Date | Name | Symbol | Type | Security | Shares | Price | Value | Ownership | Reported |
| 08/16/2023 | COMMUNITY BANK SYSTEM, INC. | CBU | Purchase | Common Stock | 1000 | $48.50 | $48.5k | | 08/16/2023 |
| 06/05/2023 | COMMUNITY BANK SYSTEM, INC. | CBU | Payment of Exercise | Common Stock | 1.8k | $53.05 | $93.9k | | 06/05/2023 |
| 05/02/2023 | COMMUNITY BANK SYSTEM, INC. | CBU | Other | Common Stock | 526.3158 | $47.50 | $25k | By 401(k) Plan | 05/02/2023 |
| 03/14/2023 | COMMUNITY BANK SYSTEM, INC. | CBU | Grant | Common Stock | 2.3k | $0.00 | $0 | | 03/14/2023 |
| 03/14/2023 | COMMUNITY BANK SYSTEM, INC. | CBU | Grant | Stock Option | 8.6k | $54.06 | $462.9k | | 03/14/2023 |
| 03/08/2023 | COMMUNITY BANK SYSTEM, INC. | CBU | Payment of Exercise | Common Stock | 517 | $61.05 | $31.6k | | 03/08/2023 |
| 06/06/2022 | COMMUNITY BANK SYSTEM, INC. | CBU | Payment of Exercise | Common Stock | 1.6k | $67.17 | $106.9k | | 06/06/2022 |
| 03/15/2022 | COMMUNITY BANK SYSTEM, INC. | CBU | Grant | Common Stock | 1.5k | $0.00 | $0 | | 03/15/2022 |
| 03/15/2022 | COMMUNITY BANK SYSTEM, INC. | CBU | Grant | Stock Option | 6.2k | $72.51 | $447.1k | | 03/15/2022 |
| 03/15/2022 | COMMUNITY BANK SYSTEM, INC. | CBU | Grant | Stock Option | 6.2k | $0.00 | $0 | | 03/15/2022 |
| 03/04/2022 | COMMUNITY BANK SYSTEM, INC. | CBU | Payment of Exercise | Common Stock | 265 | $72.94 | $19.3k | | 03/04/2022 |
| 06/10/2021 | COMMUNITY BANK SYSTEM, INC. | CBU | Grant | Common Stock | 10.8k | $0.00 | $0 | | 06/10/2021 |
| 06/10/2021 | COMMUNITY BANK SYSTEM, INC. | CBU | Grant | Common Stock | 2.7k | $0.00 | $0 | | 06/10/2021 |
| 06/10/2021 | COMMUNITY BANK SYSTEM, INC. | CBU | Grant | Stock Option | 11.7k | $80.01 | $937.2k | | 06/10/2021 |