In August 1999, the people of East Timor voted overwhelmingly against a proposal that would make their island an autonomous province of the Republic of Indonesia. The international community expected that the establishment of a new state would be straightforward. This was because it appeared that all of the factors needed for a successful transition from conflict to peace and stability were present. The reality, however, proved different which is why Timor-Leste serves as a good case study for those interested in postconflict reconstruction and specifically security sector reform. This study builds upon the themes presented in Armstrong and Chura-Beaver’s study, Harnessing Postconflict Transitions: A Conceptual Primer (2010), and Practitioner Frameworks on the Host-Nation Role in Transition to Determine how Countries Contribute to their Own Security Transitions (2010).