Teaching is characterized by contradictory demands, resulting in teaching dilemmas. For example, to promote the continuous learning of students, teachers need to set up rules and control them, which in turn can undermine students' intrinsic motivation. Teachers have to become aware of these contradictions and need to understand that not all aspects of good teaching can be maximized at the same time. An adequate representation of the dilemmatic nature of problems of teaching is therefore crucial for judging different teaching situations. Also, an adequate epistemological understanding is needed. We assessed student teachers' (N = 122) perceptions of demands in teaching in general and in regards to specific situations, as well as their epistemological beliefs. Perception of demands in general influenced the judgment of specific situations, but there was also a situation-specific component. Epistemological beliefs were related to the perceptions of demands in general, especially in situations in which the dilemmatic content was highly visible. Together, findings suggest that epistemological beliefs shape the perception of demands in teaching in general, and that the perception of demand in general again influences perception in specific situations.