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The imminent enlargement of the EU to as many as twenty-seven member states in the near future will pose severe budgetary, administrative, and operational challenges for the current member states. However, the challenges of enlargement, as great as they are, pale in comparison with the challenges of accession that will be faced by the new member states, especially those which until a decade ago were governed by Communist parties that presided over centrally-planned and predominantly collectivized economies. This paper explores five of the most critical challenges that will face the new member states of post-Communist Europe: 1) administering the acquis; 2) deepening and extending the reform and transformation of the economy; 3) reducing the high levels of unemployment and large government, trade, and current account deficits; 4) financing accession in the face of the EU’s budgetary constraints and financial provisions; and 5) coping with all of those challenges in the face of low levels of support for enlargement in a number of the current member states and high levels of ambivalence about membership in most of the candidate countries.