Current challenges in the educational sector along with age-related changes during early adolescence contribute to an increased sense of school alienation among students. Across a wide array of student behaviors, the failure to participate in classroom as well as socially deviant behaviors can be viewed as some of the central concerns associated with school alienation. This study examined the change in and cross-lagged relationships among alienation from learning, teachers, and classmates, and different self-reported learning and social behaviors across 508 secondary school students spanning a 1-year interval from Grade 7 to Grade 8. The results revealed a slight increase in school alienation and a decline in classroom participation. Earlier school alienation predicted students' later in-class participation and delinquent behavior, but not vice versa. The three alienation domains were shown to have different relationships with targeted learning and social behaviors: Alienation from learning and from teachers negatively predicted student classroom participation. Alienation from teachers and from classmates contributed to subsequent delinquent behavior. The study results emphasized the importance of school alienation for students' participation in classroom activities as well as in disruptive behaviors. Theoretical and practical implications of the findings for educational research and practice are discussed.