This article explores the relationship between security sector reform (SSR) and democratic transition in post-conflict contexts, drawing on Kosovo as a case. The study focuses in particular on the justice sector in Kosovo, reviewing the ways in which security, the rule of law and democracy have been intertwined. The article first outlines the context of the international mission in Kosovo, before proceeding to consider how the objectives, needs and constraints of different actors have influenced the reform of the security institutions and the democratization process. Thereafter, it discusses the concepts of SSR and democratic transition, briefly reviewing the UN discourse and record in SSR-related activities. Finally, it explores the interplay of these factors in the Kosovo justice sector reform process. The main finding stemming from this analysis is that not only do SSR and democratization agendas interfere with each other, but measures adopted to cope with security challenges related to the post-conflict context can also affect them both. Furthermore, this finding demonstrates that a welldeveloped UN theoretical discourse is still not matched by the reality of UN practices in the field.