This study examines semester schools, which have elements associated with transformative learning, and an adolescent population, where transformative learning has less commonly been studied. We administered the Learning Activities Survey pre/post semester (n = 173) and followed the survey with semistructured interviews (n = 30) to assess whether students experienced Mezirow's stages of transformative learning and achieved perspective transformation. Our results suggest that adolescents experience the stages of transformative learning more frequently at semester schools than at their originating schools. However, while students said they achieved perspective transformation on the surveys, interviews revealed that the outcome might better be described as a cycle of identity formation. Students said that the relationships with teachers and students, time for reflection, and the structure of the semester were important to their learning. Specifically, a supportive but challenging environment provided content that they reflected on to gain insight into their values and beliefs.