Few studies with respect to grade retention and school-disruptive behavior have focused on adolescence. Moreover, previous retention research has ignored multilevel issues. This study aims to fill these research lacunae by addressing the role of grade retention in adolescent students' school misconduct. Furthermore, we explore the role of the percentage of retained students at school in individual-level school misconduct and in moderating the relationship between retention and misconduct. Multilevel analyses of data (2004-2005) from 11,872 students in 85 Flemish secondary schools suggest that, while students retained in primary education exhibited less school misconduct in adolescence, those retained in secondary schools were more likely to break rules. Furthermore, students attending schools with a higher percentage of retainees were found to be more deviant. However, schools' retention composition moderated the relationship between grade retention and school misconduct. Implications are discussed.