An increasing number of German schools have suspended teacher-directed learning (TL) in favor of self-directed learning (SL) modules. We used the broaden-and-build theory and self-determination theory as a theoretical framework to determine whether students in self-directed and teacher-directed learning environments differ in the interplay of positive emotions and learning strategies of students in secondary education. The study also compares the mediating role of autonomy support on the relationship between positive emotions and learning strategies. Questionnaire data from 787 German secondary school students in the sixth and seventh grades were analyzed. The results of the latent mean comparison indicated that students in the self-directed learning environment demonstrated more adaptive learning behaviors. Further, a multigroup structural equation model identified strong differences in the interplay of the variables between students in the self-directed and teacher-directed learning environments. In the teacher-directed learning environment, autonomy support was not found to mediate the relationship between positive emotions and learning strategies.