Disclosed herein are systems and methods for dynamically generating menu items in response to a user selection of text in a scripting interface based on a context associated with the text and metadata associated with the text. Using the techniques disclosed herein, a computing system generates one or more menu items in a pop-up menu in response to a selection (e.g., right-click) of text. The computer system enables user customization of the menu items 132 aggregated on the pop-up menu 130, such that the user customization includes defining the task executed by a menu item in response to being selected from the pop-up menu and defining conditions in which the menu item may be generated in the pop-up menu. In some embodiments, machine-learning techniques may be implemented by the computing system to dynamically identify selection trends and predict suitable menu items to propagate on the pop-up menu.