Teachers' learning and occupational well-being is crucial in attaining educational goals both in the classroom and at the school community level. In this article teachers' occupational well-being that is constructed in teaching-learning processes within the school community is referred to as pedagogical well-being. The article focuses on exploring teachers' experienced pedagogical well-being by examining the kinds of situations that teachers themselves find either empowering and engaging or burdening and stressful in their work. The study aims to: (1) identify the primary contexts of teachers' experienced critical incidents of pedagogical well-being; and (2) determine the kind of action strategies teachers have adopted in these contexts when they are reported as empowering and engaging. The study included data collected from the teachers of nine case-schools around Finland. Altogether, a selected group of 68 comprehensive school teachers, including both primary and secondary school teachers, were interviewed. Our results suggested that interaction with pupils in socially and pedagogically challenging situations constitutes the core of teachers' pedagogical well-being. Success in both the pedagogical goals and more general social goals seem to be fundamental preconditions for teachers' experienced pedagogical well-being. Further investigation showed that teachers' approaches to socially challenging situations varied. Results suggest that teachers' pedagogical well-being is centrally generated in the challenging social interactions of their work. Moreover, the way in which a teacher acts in the situation is found to be a regulator for experienced pedagogical well-being. (Contains 1 table and 1 figure.)