A system for generating windows arrangements for a display is disclosed, which includes a processor and a computer-readable medium storing instructions for controlling the system to perform receiving a first user input requesting to generate windows arrangements for a display; in response to receiving the first user input, identifying, based on contextual information with respect to applications, a group of the applications to be included in the windows arrangements for the display; generating, based on display information of the display and the contextual information with respect to the applications, the windows arrangements, each windows arrangement providing a different on-screen arrangement of a plurality of windows associated with two or more applications of the group and defining a size and position of each of the windows on the display; and displaying a selectable list of the windows arrangements for the display.