This dissertation looks at the regime outcome in the Yugoslav successor states from 1990 to 2020. It examines how civil society, state structures, and the elite influence the trajectories of Croatia, North Macedonia, Serbia, and Slovenia after the end of socialism. First, I explore whether classes, an independent civil society, and independent state structures matter for democracy by conducting a cross-sectional time-series analysis on 13 post-communist countries. The findings reveal that an independent civil society and non-captured state structures are positively associated with democracy; in contrast, the working class seems irrelevant for the post-socialist democratisation process. Second, based on the results of the large N-analysis, case studies open the black box and examine the interaction between the state, civil society, and the elite. The qualitative analysis is based on extensive primary and secondary data collected through field research conducted in Croatia, North Macedonia, Serbia, and Slovenia over the 2018-2019 period. As the quantitative analysis does not incorporate the role of the elite, case studies reveal under which elite context agency mattered. The qualitative analysis also reveals the impact of the European Union on domestic conditions, paying special attention to timing and context. The study finds that no factor alone explains the occurrence of democracy. Democracy cannot be achieved without combining the following factors: an autonomous civil society, a non-captured state, and ruling elites willing to implement democratic reforms. In a similar vein, the analysis provides evidence that the only sufficient condition is non-captured state structures. State capacity, therefore, plays a central role in democratisation. Institutional reforms can therefore not be implemented without an independent bureaucracy. At the same time, EU conditionality can help to increase state capacity, especially when reform-willing elites are in power. EU conditionality can, however, also have unintended negative effects by fortifying illiberal governments. The other crucial variable, civil society, is not sufficient for democracy when considered alone. Interpreted this way, civil society organisations, trade unions or NGOs, need independent state structures and reform-willing elites that govern the country to lead to democracy. Lastly, the qualitative analysis shows that agency does play a role. Not for democracy, as for that one needs favourable structural conditions, but at least for the absence of autocratic regimes, the presence of reform-willing elites is crucial. Yet, the analysis also reveals agency limits. In the absence of autonomous civil society and autonomous state structures, elites have few possibilities to implement reforms and are likely to find themselves trapped in a never-ending limbo of hybrid regimes with chances and actual instances of democratic backsliding.