A method includes displaying, on a display, first content and a representation of second content associated with the first content. The method includes detecting, via one or more input devices, a user input at a location of the representation of the second content. The method includes, in response to detecting the user input at the location of the representation of the second content, in accordance with a determination that the user input includes a stylus contact, displaying, on the display, a drawing user interface including the second content and a toolbar region with a plurality of drawing tool selection affordances. The method includes, in response to detecting the user input at the location of the representation of the second content, in accordance with a determination that the user input does not include a stylus contact, forgoing display of the drawing user interface.