During Operations Iraqi Freedom (OIF) and Enduring Freedom (OEF), more than half of the U.S. personnel on the ground were civilian contractors. Unfortunately, lack of contractor oversight led to significant levels of waste, fraud, and abuse. To address these concerns, Congress created the Commission on Wartime Contracting to develop recommendations to study the acquisition process during OIF/OEF. Concomitantly, the Office of Federal Procurement Policy issued a policy letter to provide strategic-level guidance to federal agencies to assess risk and accountability when outsourcing critical functions. This Paper looks at these recommendations and guidance and identifies the gap between what has been adopted versus what was recommended—ultimately focusing on the steps needed for the U.S. military to change its culture and make government contracting a core competency for civilian and military personnel.