A method, system, and medium are provided for supplying contextual help to a user of an application. A problem encountered by the user while using the application is identified in real time. Identifying the problem may include identifying the current user task, based at least on application checkpoints encountered by the user. In response to identifying the problem encountered by the user in real time, the user is provided with short-term help and long-term help that address the problem. The short-term and long-term help may be identified based at least in part on mappings that associate user tasks with help information applicable to the user tasks.