Research has identified successful transitions from middle to high school as critical for students’ academic success. Identifying risks and protective factors associated with challenge or success in the early years of high school is crucial, especially for African American students who are disproportionately represented in the ranks of adolescents who underachieve in academics, receive school discipline sanctions, and drop out of high school. The present study examined risks associated with perceived discrimination and the protective function of school racial support and two aspects of African American adolescent identity (identification with academics and racial centrality). This study followed a sample of 46 low-achieving African American students through the first 2 years of high school. Findings showed that over and above the negative influence of discrimination and levels of ninth-grade classroom engagement, students’ identification with academics in the ninth grade was a strong predictor of tenth-grade classroom engagement. This finding points to the promise of identification with academics as a protective factor which could help adolescents reach their academic potential.