The present invention provides a system or method for displaying rich presentation taskbar buttons for a corresponding application. In one example, the rich presentation taskbar button may receive content from an application through a programming interface. The present invention further relates to a system and method for displaying a rich presentation taskbar button and for displaying and/or dismissing a thumbnail of an application window associated with the rich presentation taskbar button. The present invention may further include a system and method of pinning the thumbnail on a display or dismissing a thumbnail. The present invention also relates to a system and method for displaying multiple taskbar buttons in a taskbar including controlling the size of individual taskbar buttons, consolidating taskbar buttons and placing taskbar buttons into an overflow based on the type of taskbar button in the taskbar.