Basic education has two main goals: to promote high quality learning outcomes and pupils' personal growth and well-being. The interrelated nature of learning and well-being is here referred to as pedagogical well-being. In this study, we explore Finnish comprehensive school pupils' (N = 518) experienced pedagogical well-being by examining the kinds of situations that pupils themselves find either highly positive or highly negative during their school career. Pupils' pedagogical well-being is empirically examined in two complementary aspects: (1) determining the point in the pupils' school career in which the critical incidents are situated and (2) identifying the primary contexts of pupils' experienced critical incidents of pedagogical well-being. Results showed that critical incidents for pedagogical well-being reported by the pupils were situated all along their school career. A variety of episodes causing empowerment and satisfaction, as well as disappointment and anxiety, were reported by the pupils. Pupils perceived the social interactions within the school community as being the most rewarding as well as the most problematic part of their school career.