Abstract: In a method for displaying tailored advertising in response to user media playback behavior, an ad engine detects media playback by a user. The ad engine retrieves an advertisement rule associated with the user. Following retrieval of the advertisement rule, the ad engine analyzes the content associated with the media playback and queues user tailored advertisements based on the analyzed content and the advertisement rule. The ad engine then displays an advertisement in response to detecting a pause in the media playback in a content provider-based software application.