Police stops often perpetuate racial disparities in academic outcomes, yet few studies have examined factors that mitigate these negative consequences. Using two longitudinal studies (Study 1: n = 483, M-age = 12.88, 53% males; Study 2: n = 131, M-age = 15.11, 34% males), this article tests whether parental and school cultural socialization reduced the negative associations between police stops and youth's school engagement. Results showed that youth with police encounters reported lower school engagement. Parental cultural socialization conferred protection in one study, while school cultural socialization was a protective factor in both studies. The implications of this work stand to benefit those working to reduce the negative links between policing and African American youth's school engagement.