The article discusses the nature of the EU's political conditionality in the Western Balkans, and the effort of the EU to manage the diversity of bilateral agreements in a small space with a mixed record of compliance. The Western Balkan region reveals special trends in the EU's handling of the strategy of political conditionality, and some creeping contradictions and dangers are beginning to reveal the changing nature and the limits of conditionality. More specifically, the EU (a) is adding further, yet necessary, political conditions and criteria to weaker or more reluctant partners and emphasizes the 'journey' rather than the outcome of accession, affecting the credibility of the strategy; (b) is blending together normative, functional and realpolitik claims in the choice of its conditions, affecting the clarity of its intentions; (c) is pursuing, in some cases, a rigorous assessment of compliance and, in other cases, a more adaptable and pragmatic assessment, affecting the consistency of the process. These Western Balkan trends are bound to become more pertinent in future cases, as the EU gets more involved with other more difficult states in its eastern and southern periphery, and where the carrot of membership will be either very distant or irrelevant.