A pedagogical dilemma occurs when an in-class event or external factor challenges a teacher's principles or instructional practices and compels the teacher to resolve the dilemma. This article focuses on how resolving dilemmas can enhance the conceptual understanding of both student teachers and their supervisors. The supervisory setting this article describes--university instructors in Japan supervising preservice and in-service teachers--has not been extensively researched. The article presents three case studies: two on supervising preservice teachers and one on supervising an in-service teacher. Although approaches to supervision emphasize the facilitative aspect, the case studies of the preservice teachers exhibited circumstances more conducive to a directive-oriented approach. Nevertheless, with the assistance of the supervisors, the preservice teachers were able to develop episodic knowledge of pedagogical concepts through navigating the dilemmas they experienced. The case study with the in-service teacher, on the other hand, required a more facilitative approach to supervision. It suggests that the supervisor should understand and accommodate the pedagogical concepts under which the teacher operates to provide useful support in resolving classroom-based dilemmas.