The Copenhagen European Council in December 1993 not only gave the green light to enlargement with the CEECs, but also laid down the requirements which the associate countries should satisfy in order to become members. Over the last twenty years enlargement has become one of the most successful policies of the Union. Although the academic literature concerned with the effectiveness of the EU influence on applicant states has stressed the importance of domestic politics (Schimmelfennig and Sedelmeier, 2004; Hughes et al, 2004; Dimitrova and Toshkov, 2009), the analytical frameworks aimed at investigating the factors shaping the dynamics of EU enlargement policy have neglected the impact of the EU hopefuls. In order to address this gap in the literature the paper investigates how the profile of the candidate countries can influence EU conditionality by looking into the following two aspects: 1) the impact of problematic issues and reform challenges, which the applicant states need to address, on the scope and range of the EU conditions; and 2) the implications of the existence or lack of group dynamics for the development of the EU’s incentive structure. The study, which draws on extensive interviews with senior EU and national officials and examination of key EU documents, concludes with a reflection on the relevance of multi-dimensional approaches to investigating the evolution of EU enlargement policy.