A contextual pop-up menu of frequently used commands is displayed by an application whenever a user carries out a particular action. The contextual menu appears at the location of a cursor, so that the displayed commands are spatially very close to an item on which an action is to be performed. The commands which are displayed in the contextual menu are not limited to those provided by an application associated with the selected item. Other commands, such as system level commands, for help items or other types of user assistance features, can be added to the menu before it is displayed to the user. In addition, plug-in modules can be employed to provide other commands associated with the selected item.