Although the government's reliance on contractors to support military forces is t a new phemen, the degree to which contractors are involved in Operations Enduring Freedom and Iraqi Freedom (OIF) has increased substantially. In OIF in particular, contractors perform a wide range of services in support of stabilization and reconstruction efforts. Perhaps the most controversial and arguably the most troublesome of these contractors are those that are armed and use violence in the course of fulfilling their contractual obligations. This thesis explores whether or t such contractors, herein identified as private security providers (PSPs), have a destabilizing influence on United States political and military objectives. In doing so, the thesis identifies and evaluates the legal environment in which PSPs operate the intersection between PSP activities and critical requirements and vulnerabilities of coalition forces and PSP involvement within logical lines of operation within Iraq. In concluding, the author posits that PSPs have a destabilizing impact on t only the political and military mission, but the United States military as well. Finally, the author provides recommendations for employing PSPs in the present and future conflicts.