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This study examines the extent to which self-expression relates to engagement in the high school classroom and illustrates how teachers create classroom contexts in which opportunities for self-expression are highly engaging. Contextualizing self-expression as central to both identity formation and student engagement, this mixed-methods research draws on surveys with over 1100 students, case studies of five classes, and interviews with thirty-three students. Finding that students are more engaged in classes where they perceive more opportunities for self-expression, this work also provides an in-depth look at effective classroom contexts for self-expression, concluding that self-expression is most engaging when it is varied, content-based, autonomous, and situated in psychologically safe learning environments.