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The present study examines transition patterns of Swiss secondary and tertiary school students. Switzerland's highly canalized education system allows us to test how tracking affects person–environment fit of students for students who choose a normative versus unexpected downward transition pattern. In addition, we investigate how self-efficacy expectations and personal values affect an unexpected transition choice. Results indicate that students with strong expectancies and personal values can oppose institutional norms and chart their own academic course; however, these students are less likely to perceive a good fit between their own interests and competencies and institutional demands after the transition. Our findings underscore the importance of developmentally appropriate educational environments and systems permeable enough to adapt to developing students' changing interests.