In bilateral relations and negotiations with the European Union (EU), smaller and economically weaker states are often unable to express their national preferences. Despite their limited bargaining power, however, some Eastern Partnership (EaP) countries obtained significant concessions from the EU. This article analyzes the factors that explain EaP states’ unexpected negotiation success in the context of the Deep and Comprehensive Free Trade Agreement (DCFTA) with Ukraine, the Comprehensive and Enhanced Partnership Agreement (CEPA) with Armenia, and enhanced economic partnership with Belarus. We identify negotiation strategies that are crucial to understanding of the puzzle.