The current study examined the developmental trajectory of same-race friendship preference of racially/ethnically diverse students over the course of middle school. Participants were African American, Asian, Latinx, and White youth recruited at the start of middle school in 6th grade (N = 4,361; M[subscript age] = 11.33 years) and followed across the 3 years of middle school. School racial/ethnic diversity and the racial/ethnic representation of students in their academic classes, including honors classes, were examined as predictors of friendship preferences over time. Results from latent growth curve models revealed that same-race friendship preference increased over the course of middle school and was shaped by both the school and classroom racial/ethnic context, above and beyond availability. Greater school racial/ethnic diversity predicted steeper increases in same-race friendship preference over time for all racial/ethnic groups. However, there were interactions involving race/ethnicity when the analyses focused on how students were represented in their academic classes compared with school. African American and Asian youth who were underrepresented in honors classes showed steeper increases in same-race friendship preference over time. Implications for prejudice reduction and creating more inclusive school environments are discussed.