The voluminous literature on recent transitions to democracy has generally lacked an analysis from the perspective of international law. This article explores four aspects of efforts to promote a normative ‘democratic entitlement’. First, it reviews the ways in which notions of democratic legitimacy have infiltrated virtually every aspect of international legal discourse. Second, it explores how a normative legitimacy standard may alter foundational doctrines of international law, such as non-intervention and the recognition of states and governments. Third, it reviews arguments against the emergence of ‘democratic entitlement’. These arguments both take issue with the sources of law relied upon by the entitlement's proponents, and ask whether the substantive and procedural aspects of democracy implicit in the democratic entitlement thesis are conceptually coherent. Finally, the article explores the ways in which a legal analysis of democratization confronts questions not addressed by the methodologies of other disciplines.