The establishment of a Cooperation and Verification Mechanism for monitoring Bulgaria’s and Romania’s progress in the areas of judiciary and fight against corruption not only confirms the evolutionary nature of EU conditionality, but introduces a new feature, that of post-accession conditionality. More than three years after accession, neither Bulgaria nor Romania have managed to tackle the remaining issues and the scrupulous monitoring mechanism is still maintained. What are the main features and limitations of post-accession conditionality? Why does the effectiveness of EU conditionality deteriorate after accession? The article outlines a conceptual framework for comparative study of pre-accession and post-accession conditionality. On the basis of a stage-structured conditionality model, it discusses the transformations of the main elements of conditionality before and after accession and argues that the absence of accession advancement rewards combined with toothless explicit threats for sanctioning non-compliance produce very weak negative incentive structure which undermines the effectiveness of post-accession conditionality. The study, which draws on extensive interviews with senior EU officials and examination of key EU documents, highlights the growing application of differentiated and targeted conditionality and concludes with a reflection on the future of the mechanism and its implications for the ongoing enlargement of the Union with countries of the Western Balkans and Turkey.