Abstract: A Cooperative Help Assistance (CHA) system and method provide real-time user assistance for one or more windows-based Graphic User Interface (GUI) applications or a single application's different subsections such as web pages, running concurrently in any operating system. The CHA System enables the development of an informative assistance object independently from the original source code or development environment of the target Host Application. The assistance object can be selected by any number of user interfaces from sophisticated inference driven interactive interface search tools or categorized lists. By intercepting and monitoring user actions on a Host Application, the CHA system performs intelligent assistance in the context of the target host application program.