An assistance service through its local client application or agent at a user's device hardware and software environment information and monitor a health of one or more applications. Upon detecting an issue or being activated by the user, the assistance service may perform diagnostic and/or recovery actions. If predefined or dynamically determined recovery actions are inadequate to address the issue, the assistance service may engage a support service providing collected user device environment information and received server environment information to the support service. A history of attempted recovery actions and diagnostic results may also be provided. The assistance service may, through a user interface of its local, client or agent, facilitate communication with the supports service and perform recovery actions, suggested by the support service providing feedback to the support service. When needed, the assistance service may rollback a version of locally installed or server-side applications to address the issue.