Abstract: A content overlay system for a digital device is described. The content overlay system includes a processing module configured to monitor events of the digital device to generate data indicative of the activation of and/or use of one or more applications of the digital device. The processing module is configured to process the generated data to determine timing data indicative of when to overlay content on an active window and/or to determine what content to overlay. An overlay generation module is configured for placing an overlaid window in front of the active streaming window or application and for displaying content in the overlaid window. The overlay generation module being configured to generate the overlaid window and display content from an overlaid content server according to the determined timing data and/or determined content.