Why has an S2 never won a wargame when playing predicted enemy courses of action against a friendly course of action during the Military Decision Making Process (MDMP)? Why did the V Corps commander during Operation Iraqi Freedom (OIF) respond to a question about the threat by saying "the enemy we're fighting is different from the one we'd wargamed against "? Both these questions are troubling and lead to deeper questions about the process in developing enemy courses of action. This monograph will identify theoretical and analytical difficulties within current IPB doctrine. In addition, this document will show how these difficulties became institutionalized through Cold War realities within the Army intelligence estimate process. Historical evidence will be presented to support the claim that the identified difficulties are detrimental to Army operations in ambiguous and uncertain environments. Finally, this paper will present alternative theoretical constructs to the current IPB process for consideration in future IPB doctrine. The aim of this paper is to widen the scope of IPB doctrine to include other theoretical frameworks as tools for the Army intelligence officer and analyst as they consider the 21st Century threat facing them.