This chapter addresses the questions of what the structural characteristics of European Union (EU)–Maghreb relations are and what factors account for the global features, as well as bilateral differentiation vis-a-vis each individual country of the region in the framework of the European Neighbourhood Policy (ENP). It examines the postcolonial legacies and background of the institutionalisation of EU–Maghreb relations and the debate on the degree of interdependence or dependency that can be observed in this relationship from an international political economy perspective. The chapter also examines the realist hindrances to liberal region-building and integration between the Maghreb countries and the allocation of foreign policy roles and bilateral differentiation between them in the context of the ENP. The paradoxical coincidence of two paradigmatic instances of international cooperation and conflict somehow set the tone of Euro-Maghreb relations. Two Maghreb countries, namely Tunisia and Morocco, were, along with Israel, the frontrunners in signing and implementing their third-generation Association Agreements with the EU.