Adopting a motivational perspective on adolescent development, these two companion studies examined the longitudinal relations between early adolescents' school motivation (competence beliefs and values), achievement, emotional functioning (depressive symptoms and anger), and middle school perceptions using both variable- and person-centered analytic techniques. Data were collected from 1041 adolescents and their parents at the beginning of seventh and the end of eighth grade in middle school. Controlling for demographic factors, regression analyses in Study 1 showed reciprocal relations between school motivation and positive emotional functioning over time. Furthermore, adolescents' perceptions of the middle school learning environment (support for competence and autonomy, quality of relationships with teachers) predicted their eighth grade motivation, achievement, and emotional functioning after accounting for demographic and prior adjustment measures. Cluster analyses in Study 2 revealed several different patterns of school functioning and emotional functioning during seventh grade that were stable over 2 years and that were predictably related to adolescents' reports of their middle school environment. Discussion focuses on the developmental significance of schooling for multiple adjustment outcomes during adolescence.