Engagement, Enlargement, and Confrontation provides a holistic view of the European Union’s eastern relations explored in an historical context following the end of the Cold War. The author draws out the key achievements and failures of this strategic exercise. The focus is on the institutional adaptation of the European Union as well as on the dynamics of its policies towards the East. Graham Timmins identifies four interconnected factors which have shaped the development of the EU’s policies towards its eastern neighbours; the projection of the EU’s identity as an agent of peace and stability, the maintenance of internal stability within the Union, the coordination of Member State foreign policies, and the EU’s relations with Russia. The book explores the key challenges faced by the European Union in terms of the EU’s eastern policies. These include capacity building, the management of expectations in the eastern neighbourhood, the reconciliation of national perspectives and agendas with wider EU strategic thinking, and last but not least the handling of the relationship with Russia. The general conclusion of the study is that the EU’s internal development in respect to its relationship with its eastern members and neighbours is likely to remain complex and unpredictable.