This book takes a systematic and holistic approach to examining all 41 peacemaking initiatives used to settle the Cyprus question from 1955 onward under the auspices of the United Nations and or other actors in the international system, including the United States, Canada, the UK, Greece and Turkey. The analysis of peacemaking strategies, dynamics and obstacles fleshes out numerous relationships (i) peacemaking processes, dynamics and outcomes, from signaling to negotiations and to post-accord completion and implementation; (ii) concessions, constraints and leverage during peacemaking negotiations and third party mediation; and (iii) obstacles to finding an endgame solution and satisfying conditions for lasting peace expectations that all parties can agree on and implement successfully. After documenting 62 interviews with top political leaders in Cyprus (including top tier elected elites and third party mediators) and about 70 more interviews with key informants (including academics, researchers, members of negotiating teams, technical committees and working groups), this book concludes with a plethora of descriptive, as well as prescriptive, propositions on how peacemaking processes could lead to more sustainable and implementable peacemaking initiatives in Cyprus and in similar protracted and seemingly intractable cases.