This chapter analyses the major challenges AMISOM faced in trying to develop and implement a successful exit strategy. It begins by summarizing the different modes of exit that are usually available to peace operations and discusses how some of these occurred in earlier foreign military operations in Somalia since the early 1990s. It then examines the evolution of AMISOM’s exit strategy as articulated in various official documents. Five major challenges to implementing a successful exit strategy are discussed in the third section, while the conclusion briefly summarizes how, by mid-2017, AMISOM had developed a framework agreement to guide the handover of the lead security role to Somali security forces.