Adolescents with juvenile justice system experience may be enrolled into alternative schools to increase academic success or to reduce delinquency. This study used longitudinal data on a racially/ethnically diverse sample of 1,216 male, first-time adolescent offenders to examine how youthful offenders’ school experiences were associated with academic outcomes, school attitudes, and delinquency. Effects varied by domain in important ways. Youth who attended alternative schools generally fared better academically than youth who attended traditional schools. However, importantly, youth who attended alternative schools subsequently engaged in more delinquency and violent reoffending than youth in traditional schools. The findings indicate that disrupting normative schooling appears to be the most detrimental to youth outcomes across domains.