The entry introduces the concept of a legal dilemma as a term of art. Specifically, the concept of a legal dilemma, as understood and construed in this entry, refers to an unavoidable and irresolvable conflict between norms of international law. The entry unpacks and explains the various elements of this definition. It also presents and discusses various strategies to deal with legal dilemmas once they have arisen. Since the concept of a legal dilemma is a stipulative concept, the entry concludes by justifying the concept’s existence and by identifying the merits of dilemmatic legal thinking.