This study investigated whether parental racial socialization practices moderated the relation between racial discrimination in school and adolescents’ educational outcomes. Using data from a longitudinal study of an economically diverse sample of 630 African American adolescents (mean age = 14.5) from a major East Coast metropolis, the results revealed that cultural socialization attenuated the effect of teacher discrimination on grade point average (GPA) and educational aspirations, as well as the effect of peer discrimination on GPA. Also, preparation for bias and cultural socialization interacted to make unique contributions to African American adolescents’ educational outcomes. Finally, there was some evidence that teacher discrimination was more detrimental to the academic engagement of African American males than females. Implications for research and practice are discussed.