In the past ten years, the long-standing trade relations between the European Union (EU) and the African, Caribbean, and Pacific (ACP) countries have experienced radical transformations. The negotiations of the Economic Partnership Agreements (EPAs) between the EU and seven regional groupings formed by the ACP countries have led to the EU being maneuvered into an unexpectedly weak position. For the first time, European negotiators had to substantially leave their pre-agreed negotiation path and positions due to the immense pressure from ACP countries, regional organizations, and non-state actors – and still have not been able to finalize negotiations that had initially been expected to only take five years until the end of 2007. These developments constitute a two-tire puzzle: Not only could the EU not play its ‘negotiation game’ and largely determine the outcomes of negotiations, but also did the outcomes of the negotiations differ between the individual regional negotiations groups despite a single European mandate for all seven regionally conducted EPA negotiations. The paper argues that a comparative ‘outside-in perspective’ from the ACP countries’ side towards the EU is essential to understand the puzzling EPA negotiation process and its (preliminary) outcomes. More specifically, it argues that the negotiations were rather determined by regional dynamics, different negotiation structures of individual EPA configurations, and the role of regional hegemons than by the EU’s actions and positions. This perspective has so far gained little attention. Trade negotiations with the EU have largely been illustrated as a clear-cut case in most studies and it is to be questioned to what extent the EPA negotiations challenge such a scenario. The paper presents a comparative case study on the EPA negotiation groups of the Southern African Development Community (SADC) and the East African Community (EAC) from a ‘South-Eastern African perspective’.