Over the past ten years the United States has relied on private contractors to support military forces and rehabilitate national infrastructures in Somalia, Bosnia, Kosovo, Afghanistan, and Iraq. Though contractors are essential to such post-conflict operations, the U.S. government’s management and oversight of outsourced support remains critically deficient. As the United States builds its institutional capacity for long-term post-conflict reconstruction, it will need to outsource tasks to specialized private firms and non-profit organizations more strategically, efficiently, and transparently. This paper assesses the ramifications of post-conflict outsourcing in four sections. The first section provides a brief history of outsourcing in military and reconstruction operations. The second analyzes the benefits of private contracting arrangements. The third considers pitfalls of the current U.S. outsourcing system, which include inefficiencies as well as more serious security threats. The final section concludes with policy recommendations to improve management systems in the context of post-conflict operations.