A method for contextual graphical user interface (GUI) training includes, with a training module, switching from a normal mode of the GUI to a lesson mode to provide a lesson to a user, the lesson being one of a number of lessons that were preselected by the user. The method further includes, while in the lesson mode, overlaying instructions of a task onto the GUI, with the training module, providing example user input to demonstrate the task, with the training module, undoing the task, prompting the user to perform the task, notifying the user that an input received by the computing system does not correspond to the demonstrated task, and recording completion of the task in response to input from the user, the input corresponding to successful completion of the demonstrated task.