ASEAN is a well-known regional organization of extraordinary diversity, encompassing both democracies and authoritarian states. Interest in and participation in United Nations peacekeeping operations (UNPKO) varies widely among ASEAN members. The purpose of this chapter is to illustrate the multifaceted nature of the Southeast Asian countries’ contributions to UNPKO and to present the specifics of their peacekeeping practices as they emerge from different historical and international contexts. First, this chapter provides an overview of the current state of the UNPKO. Second, it explains why ASEAN countries became interested in UNPKO and contributed their personnel (troops, police, experts on mission, and staff officers). The author attempts to include their historical background, political and economic motives, characteristics of their deployments, and limiting factors. Finally, the author assesses how ASEAN members portray their peacekeeping activities and examines the motivations behind their decisions to seek greater political legitimacy and leadership at both the regional and global levels.