Emphasizing Poland and its relations with Ukraine, this paper applies a Europeanization framework to examine the uploading of external relations policies by EU members. It argues that as enlargement has shortened the list of countries to which the EU has made membership commitments, normative entrapment will not be at work in its external relations, nor address the more fractious nature of EU decision-making brought on by a larger and more diverse membership. This results in strategic behaviour by EU members and more laboured decision making, which can be expected, in general, to complicate the EU's external relations. Simply put, the coalition building that is so central to EU policymaking is more difficult following the eastward enlargement. However, because the new members vote, collaborate, and build coalitions in favour of closer ties to these eastern neighbours, complications from enlargement should be far less pronounced in the eastern policy than with other ENP countries. This comes despite striking shortcomings by Poland in the administrative capacity and elite socialization that normally characterize those member states who often succeed at projecting their preferences onto EU policy. All of this means that one can expect an eastward shift in the focus of the EU's external relations, and a deepening of its differentiated approach to external relations.