In this CPA Working Paper, Payton L. Knopf, a former Council on Foreign Relations fellow and current Foreign Service officer, discusses the importance of developing innovative diplomatic strategies for evaluating U.S. engagement with nonstate armed groups (NSAGs). He argues that the administrations of both George W. Bush and Barack Obama have sought to broaden the State Department's mission beyond state-to-state diplomacy. However, little work has been done to prepare U.S. diplomats for analyzing and engaging with NSAGs, often the most influential nonstate actors. Taking into account the basic challenges that confront U.S. engagement with these groups, Knopf calls on the State Department to develop clear guidelines as to why, when, and how its diplomats should conduct such outreach. His proposed framework for this decision process has a three-phase process: developing a profile of the NSAG, defining U.S. government objectives toward the group, and conducting a cost-benefit analysis. The timing for engagement, in Knopf's view, should be determined by when it is best suited to achieve U.S. objectives rather than near-term timelines. Finally, Knopf stresses that several bureaucratic and operational reforms are necessary to allow the State Department to execute this increasingly important mission.