In light of the rise of democratic backsliding and illiberal trends in Europe’s East, this paper critically examines the enduring effectiveness of EU enlargement as a tool for external democracy promotion. Revisiting the debate on democratic conditionality and its limits, it argues that incentive-driven democratisation has failed to develop the necessary traction to foster deep and sustainable democratisation among aspiring member states. Quite to the contrary, current developments confirm two main concerns held by scholars of EU enlargement: on the one hand, several of the former frontrunners from Central and Eastern Europe are experiencing a delayed form of post-accession rollback of reforms. On the other, similar trends in the Western Balkans and, even more starkly, Turkey, suggest that democratic conditionality is running out of steam as a driver of domestic change. Combining cross-regional analysis with comparative insights from individual cases, the paper charts both the theoretical and practical implications of the spread of democratic backsliding for the field of EU enlargement studies.