Secessions generally entail considerable violence, since states are obviously reluctant to give up lands and react to secessionist demands deploying military force. In broad terms, this is what occurred in Kosovo. However, there are few exceptions to the rule: one is represented by the peaceful secession of Montenegro from its union with Serbia. The goal of this study is to understand which factors allowed Montenegro to achieve independence without resorting to violence, whilst Kosovar Albanians engaged in violence against the state. For this purpose, I will compare the divergent dynamics of secession in Montenegro and in Kosovo, examining the interactions among three actors: the leaders of the state (minorities wish to separate from), the leaders which claim to represent separatist minorities and external actors involved in the bargaining process. I will investigate the variations in paths to secession by analyzing competing lines of explanations and I will show how -while familiar economic, cultural and demographic factors fail to explain differences across cases- three political variables seem to be influential: first, I argue that power sharing regimes can -if not avoid secession- at least prevent armed conflict onset between minorities and the state, while the exclusion of the representatives of an ethnic group from central power increases the feasibility of a violent secession; second, the higher the commitment to democracy of the élites involved in the conflict, the higher the possibility of peaceful secession; third, the incentives and the mediation of the EU can decrease the chances of armed conflict.