Methods for configurable and proactive application diagnostics and recovery are performed by systems and devices. A diagnostics manager determines diagnostics packages corresponding to problems described in client device diagnostics requests. Session identifiers are generated and returned with diagnostics identifiers to clients which then provide the session identifiers and diagnostics identifiers to a service manager for session initiation. Diagnostics packages are located, retrieved, and provided back to the client by the service manager that invokes a client-side engine to execute diagnostics packages. Results are provided to the diagnostics system which determines additional packages to be executed by the engine during the same diagnostics session. Further, device-specific tokens are acquired by client devices which execute local diagnostic packages and acquire remote diagnostic packages for execution in the same session. Additionally, diagnostics packages provide their own user interfaces, and local packages are automatically executed upon invocation of help applications.