This paper compares the escalation of civil war in South Ossetia and Kosovo and shows how different modes of transition deeply influenced the timing and type of conflict in these two cases. It argues that regimes resulting from a transition from above – when the elite in power leads the process of regime change and imposes its political agenda on other social actors – are more likely to ensure political stability in the short term, since governments are more cohesive internally, enjoy the support of the military, and can rely on a loyal bureaucracy. In contrast, regimes that emerge from transitions from below are more likely to experience civil war with an ethnic minority in the short term because of an intrinsic weakness of the elite in power. Under these circumstances, the newcomers need to win the loyalty of the military and of the bureaucracy, and separatist groups can take advantage of the incumbents’ weaknesses and try to build resources to militarily challenge the state.