| Crystal Run Health Plan, LLC | Middletown | 4 | 2020-10-06 | Layoff |
| Crystal Run Health Plan, LLC | Middletown | 1 | 2020-08-03 | Closure |
| Crystal Run Health Plan, LLC (Phase 5) | Middletown | 1 | 2020-06-29 | Closure |
| Crystal Run Healthcare, (including Crystal Run Ambulatory Surgery Center of Middletown, LLC) | Middletown | 53 | 2020-05-04 | Layoff |
| Crystal Run Healthcare, (including Crystal Run Transformation Services, LLC and Crystal Run Healthcare Physicians LLP) | Middletown | 422 | 2020-04-27 | Layoff |
| Local Media Group, Inc. dba Times Herald-Record | Middletown | 94 | 2020-02-06 | Closure |
| Crystal Run Health Plan, LLC (Phase 4) | Middletown | 1 | 2020-01-17 | Closure |
| Crystal Run Health Plan, LLC (Phase 3) | Middletown | 4 | 2019-12-06 | |
| Crystal Run Health Plan, LLC (Phase 3) | Middletown | 4 | 2019-12-06 | Closure |
| Crystal Run Health Plan, LLC (Phase 2) | Middletown | 3 | 2019-07-29 | Closure |
| Geritrex, LLC | Middletown | 56 | 2019-05-21 | Closure |
| Crystal Run Health Plan, LLC | Middletown | 7 | 2019-04-08 | Closure |
| Crothall Healthcare (Environmental Services at Crystal Run Healthcare) | Middletown | 20 | 2018-12-17 | |
| Crothall Healthcare (Environmental Services at Crystal Run Healthcare) | Middletown | 20 | 2018-12-17 | Closure |
| NSC Wholesale Holdings, LLC d/b/a National Wholesale Liquidators (Middletown) | Middletown | 22 | 2018-10-18 | Closure |
| NSC Wholesale Holdings, LLC dba National Wholesale Liquidators (Middletown) | Middletown | 22 | 2018-10-18 | Closure |
| Greater Hudson Bank (Middletown) | Middletown | 1 | 2018-09-28 | Layoff |
| Middletown Community Health Care, Inc. (Orchard St) | Middletown | 14 | 2017-11-27 | Closure |
| Middletown Community Health Care, Inc. (North St) | Middletown | 8 | 2017-11-27 | Closure |
| Middletown Community Health Care, Inc. (Grove St) | Middletown | 8 | 2017-11-27 | Closure |
