In the wake of the integration of ten Central and Eastern European (CEE) countries into the European Union (EU), enlargement was hailed as the most successful tool for external democracy promotion. Fast forward fifteen years, initial enthusiasm has given way to growing concerns over democratic backsliding among both recent EU member states and candidate countries. This paper proposes a comparative analysis of the conditions under which democratic backsliding emerges in the EU enlargement region. Its theoretical contribution consists in bringing together the external, EU-driven perspective on democratic transformation in the Post-Communist region with more domestically geared explanations focused on institutional design and voter attitudes. The paper employs fuzzy-set qualitative comparative analysis (QCA) to examine the causal pathways leading to the degradation of democratic performance or, inversely, the stabilisation of democracy in Central and Eastern Europe and the Western Balkans. Its findings feed into the broader debate on democratic backsliding as a challenge to the continued spread and sustainability of liberal democracy.