The conflicts in Afghanistan and Iraq have spurred discussion and thought concerning the dilemma of finding a suitable exit strategy. Expeditionary Economics is one of the theories under development that may provide a viable solution by building economic capacity in struggling nations. The objective of this monograph is to examine the use of U.S. military forces serving a lead role in the employment of expeditionary economics through a case study analysis, focusing on the operational risk involved as a result of military-led economic intervention. These risks potentially pose a direct threat to the achievement of national strategic objectives due to an increased role in economic development by military forces ill-suited to the tasks. This monograph will focus on contemporary case studies that are fragile states which experienced U.S. military intervention in key strategic locations in Africa. Findings include two primary risks associated with the application of expeditionary economics through military efforts. Inaccurate and limited understandings of the local operational environment coupled with local perceptions anchored by history are realities faced by expeditionary military forces. The risks that emerge to the mission are further compounded by increasing the role of military forces to include expeditionary economics. The complexities of local economies lead soldier statesmen down a dangerous path that may take a sharp departure from their core competencies. There is a clear need to create or bolster economic initiatives in war torn regions in order to help stabilize a region; however, the tools used by the U.S. government must be sorely scrutinized. The U.S. military would benefit greatly from the council of a trained economic advisor embedded at the ground level. This advisor could help leaders understand the environment and develop a well nested plan that compliments U.S. national policy that remains within the realm of their professional means.