This article argues that ‘contested compliance’, i.e. a situation in which compliance conditions are challenged by the expected norm followers, offers an empirical access point for studying changes in the normative structure of world politics. It conceptualizes the normative structure as the ‘structure of meaning-in-use’ that works as a reference frame for decision-makers. The argument builds on a distinction between type, category and meaning of norms. In addition, the article distinguishes between a behaviorist approach to the impact of regulative and constitutive norms on state behavior, and a reflexive perspective on the impact of discursive interventions on the formative structure of world politics. The intention of the argument is twofold. First, it addresses the puzzle of good norm following despite increasingly contested norms, e.g. regarding the European Union’s accession criteria, on the one hand, and the United Nations Security Council resolution 1441, on the other. Second, it draws on and develops further the input of reflexive sociology on International Relations theory.