Technologies are described herein for providing intelligent delivery of actionable content. Metadata that describes user activities at a computer system is analyzed to determine a need for actionable content. Actionable content is dynamically delivered to one or more client consoles when need for actionable content is presented. The actionable content may be presented in a number of forms, including links to, or the delivery of, video, text and/or image content. Actionable content may also include links or deliverable environments for enabling automatic engagement of a specific application scenario. The discovery and delivery of the actionable content may be improved by the use of one or more feedback mechanisms.