Recently, a number of violent interracial interactions—between community members and public safety officers—has ignited a national debate about race, inequality, environmental/situational context, and the use of force among police and school resource officers. We investigate how perceptions of neighborhood and school safety are associated with adolescent exposure to racial discrimination. Using data from the National Survey of Child Health (NSCH) 2011–2012, we find that nonwhite youth experience greater levels of racial discrimination than their white counterparts after accounting for difference in exposure to violence and perceptions of neighborhood and school safety. Estimates from propensity score matching models show that differences in ever experiencing discrimination between safe and unsafe schools decline as perceptions of neighborhood safety increase, except in residential areas that are usually safe. Yet, black and Hispanic adolescents attending safe schools in neighborhoods that are always safe experience similar rates of discrimination as other nonwhite youth living in residential areas that are never safe. The implications for social mobility are discussed.