The European Union (EU) has encouraged democratic development in a number of post-communist states. This article examines the extent of EU involvement in Ukraine and its results. It notes that there has been a substantial disconnect between the rhetoric of Ukraine’s ‘‘European Choice’’ and authoritarian trends in the country. Ukraine signed a series of agreements with the EU, but membership in the organization was never offered. The EU’s interest in Ukraine, however, was rather meager and it never gained means to have much leverage. As authoritarianism became more pronounced, the EU began to disengage from the country. The article argues that part of the problem was that the EU never applied political conditionality to Ukraine as it had with other states. The ‘‘Orange Revolution’’ opens up new possibilities and challenges, and the EU now must come to grips with a more democratically and Western-oriented leadership.