The Ukraine crisis itself is, to some extent, the result of a flawed approach on the part of the EU to the strategic question of its relationships with its Eastern neighbours, an approach rendered more fraught by the parallel American enlargement of NATO. The EU has found itself constrained in its reaction to the Ukraine crisis by policies adopted over previous decades. In the first part, this article will situate the crisis in the historical context of the twin enlargements of the EU and NATO. Secondly, it will assess the consequences of the European neighbourhood policy in fostering the crisis. In the third part, this article will argue that, during the crisis itself, the EU acted in ways that were more constraining than enabling. Finally, the article will evaluate the EU's response in terms of the criteria laid out in the Introductory Framework to this Special Issue.