In earlier efforts by many researchers to explain the breakdown of peacemaking initiatives to settle the Cyprus question, the focus has been primarily on one or just a few initiatives. This dissertation takes a systematic and holistic approach to examining all 41 peacemaking initiatives 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. I believe that the qualitative analysis of peacemaking strategies, dynamics and obstacles (and in conjunction with various research literature) fleshes out numerous relationships between: (i) peacemaking processes, dynamics and outcomes, from signaling to post-accord completion and implementation; (ii) the relationship between concessions, constraints and leverage during peacemaking negotiations; and (iii) obstacles to finding an endgame solution that all parties can agree on, and overall obstacles that are detrimental to lasting peace in Cyprus. After concluding 62 interviews with top political leaders in Cyprus (including top tier elected elites and 3rd party mediators) and about 70 more interviews with key informants (including academics, researchers, members of negotiating teams, technical committees and working groups), this dissertation concludes with a plethora of descriptive propositions on how peacemaking processes could lead to more sustainable and implementable peacemaking initiatives in Cyprus and perhaps in similar protracted cases.