Operational contract support activities during stability and reconstruction operations rely significantly on local national contractors to provide goods and services for U.S. forces. In some cases, local national contractors are given priority in competition for contracts as a means of stimulating and rebuilding the local economy. A major risk associated with using local national contractors in contingency environments is the presence of business entities that may directly or indirectly support adversarial forces. Entering into contracts with enemy-affiliated business entities creates significant contractual and security risk for U.S. forces. Mitigating the effects of enemy-affiliated business must be a priority for contingency contracting officers. However, the process of preventing enemy-affiliated business entities from contracting with the U.S. government is complex and difficult to navigate. In this MBA Report, we analyze the reasons for this complexity and provide future policy recommendations to better counteract the contracting-with-the-enemy phenomenon.