Interest in student engagement has increased over the past decade, which has resulted in increased knowledge about this concept and about the aspects that facilitate engagement. However, as yet, only a few studies have focused on engagement from the perspective of the teacher. In this study, we capture the experiences of teachers who were explicitly working with their teams on fostering student engagement. We used the learning history method to capture those experiences and at the same time to stimulate learning within the participating teams. A learning history includes the voices of the different participants involved in order to stimulate reflection and learning. Three teams of teachers participated in the writing of this learning history. Several teachers (n = 10), students (n = 10), and managers (n = 5) from or related to the teams were interviewed. The learning history shows that, on the one hand, teachers emphasized positive relationships and structure in relation to student engagement, yet, on the other hand, students continued to provide examples of negative relationships and mentioned a lack of structure, although they also mentioned improvements. Furthermore, the learning history showed that teachers in all teams reflected on their experiences and learned from the activities employed to foster student engagement, which included taking a more positive approach, conversations about a skills form, and being more consequent. These results taken together indicate that it is possible for teachers to do a better job of engaging their students and that their repertoire can be expanded to include more engagement-related actions. Finally, the learning history produced offers insight into the difficulties experienced by the teams. An important limitation mentioned by all teams was that teachers found it difficult to address each other’s behavior when someone did not act as agreed upon.