This paper identifies six challenges facing U.S. stability operations. These include issues of policy, leadership, civil affairs force structure, assessment, joint coalition operations and resource scarcity. The identified challenges stem from both the findings of the Special Investigator for operations in Iraq and Afghanistan and from personal observations from deployments as a civil affairs operator and planner. These challenges are framed against current U.S. policy, and department of defense, department of state and interagency capabilities. Potential remedies for each of the six challenges is provided, as well as suggestions for the way ahead for U.S. stability operations.