A method and system for automatically displaying content of a window on a display that has changed orientation is described. The content of a window, such as a dialog box, that has been authored for a particular size is repositioned and resized such that the window is viewable in its entirety when the display screen orientation is changed (e.g., from portrait to landscape.) A scroll bar is added to allow full access to content that is not visible within the display screen when necessary. Likewise, the scrollbar is removed when the scrollbar is no longer necessary in the new orientation. The repositioning and resizing of the window, as well as the addition or removal of the scrollbar occurs without interruption of other operating system applications.