The present research examined the role of maladaptive self-regulatory beliefs as vulnerability factors for academic and emotional difficulties during the transition to middle school. A short-term longitudinal design was employed to follow two groups of early adolescents: 187 adolescents who experienced a school transition between the fifth and sixth grades, and 142 adolescents who did not experience a school transition between the fifth and sixth grades. Adolescents completed measures of perceptions of academic control and importance of academic success, experience of chronic academic strain, daily school hassles, and depressive symptoms. Teachers reported on students' academic engagement, including levels of helpless behavior, effort, and academic performance. Consistent with the proposed model of self-regulation, maladaptive self-regulatory beliefs (i.e., decreased perceptions of academic control and importance) predicted individual differences in perceived school-related stress and depressive symptoms over the course of the middle school transition, but were not associated with academic and emotional difficulties in adolescents who remained in a stable school environment. Moreover, a self-regulatory sequence was identified proceeding from maladaptive self-regulatory beliefs, to academic disengagement, to enhanced perceptions of school-related stress, to depressive symptoms. This study bridges prior theory and research concerning the psychological impact of normative developmental transitions, the developmental context of depression, and the associations among self-regulatory beliefs, achievement-related behavior, and emotional experience.