Recent experiences in Iraq and Afghanistan remind U.S. policymakers of the tremendous obstacles and challenges that confront states as they attempt to install liberal, democratic political institutions. The multifaceted transition process involves a host of overlapping and interrelated political, economic, and social innovations that often must be tailored to the specific historical, demographic, and regional needs of each community. While it would be presumptuous to suggest any rigid schedule or set of priorities, most scholars and policymakers agree that restructuring the security and civil-military institutions is vital to the transition. The primary focus of this analysis is a detailed examination of two earlier and successful efforts at democratization—the Federal Republic of Germany and South Africa—paying particular attention to the role of civil-military institutions. The West German and South African examples illustrate the intricate complexities and numerous considerations that factor into this process and provide some important lessons for the future. This monograph analyzes the decisionmaking process behind the construction of the German and South African armed forces in their transition to democracy, and it concludes with a brief list of policy recommendations for future efforts geared toward democratizing formerly authoritarian armed forces.