The EU enlargement, completed in 2004, has been hailed as one of the most significant EU accomplishments. It has also been called the most effective democracy promotion mechanism ever developed and applied. There is a lot of truth in such claims. The eight Central and East European countries that joined the EU have been the most successful examples of democratic consolidation and transition to a market economy in the entire postcommunist region. This paper examines the impact of the EU accession process on democratic consolidation and the consequences of EU membership on the quality of new democratic regimes in these countries. In the first part of the paper, I will review empirical evidence showing the diverging trajectories of postcommunist transformations and the deepening split between two parts of the former Soviet bloc. In the second part, I will sketch five dilemmas faced by the new, postcommunist members of the EU. These dilemmas reveal the tension between the requirements of EU membership and continuation of postcommunist transformations aimed at improving the quality of democracy and securing faster economic growth.