The Wars in Iraq and Afghanistan mark an era of unprecedented outsourcing in contingency operations. Although significant outsourcing occurred in prior wars, never has the scale been so large for so long. Counterintuitively, as outsourcing increased, the number of government acquisition personnel decreased. This led to waste, fraud, and abuse. The Commission on Wartime Contracting made several findings and recommendations to prevent future contract administration problems in contingency operations. A principal concern is that the U.S. military needs to increase the number of acquisition experts, change its culture, and treat government contracting as a core competency. In response to outsourcing concerns, the Office of Federal Procurement Policy issued Policy Letter 11-01 on the Performance of Inherently Governmental and Critical Functions. The Letter provides strategic-level guidance to federal agencies to assess risk and accountability when outsourcing. Although the Letter provides helpful guidance, it is only a first step. More is needed to prevent the contract administration failures of the wars in Iraq and Afghanistan from recurring. This Paper examines further-needed steps and ways in which the U.S. military can change its culture and make government contracting a core competency