A system for up-selling content during periods of likely viewer disinterest may include a content delivery network configured to provide media content and at least one choice of alternative content, a content viewing device, and a content processing device for interfacing the viewing device with the content delivery network. The content processing device may be configured to detect likely viewer disinterest in media content, prompt the selection of alternative content, and selectively replace the media content with the alternative content upon viewer selection. Additionally, methods for estimating a degree of likely viewer disinterest and discounting the offering price of the alternative content options are implemented by the system.