Social awareness, the “ability to understand the perspectives of and empathize with others, including those from diverse backgrounds, cultures, and contexts“ (CASEL, 2020) is a critical skill for youth in a multicultural democracy. This study explored individual and school environmental predictors of student patterns in social awareness development across middle school. Mixture modeling was used to classify students based on their patterns of social awareness development across middle school, and multinomial logistic regressions explored how student demographics, perceptions of school culture/climate, and exposure to peers from different racial/ethnic backgrounds were related to class assignment. Findings show worse developmental trajectories for males and African American, Hispanic/Latinx, and White students compared with Asian and female students, implying something needs to be done to better serve them. Positive trends in student perceptions of culture/climate (i.e., consistent positive or improving perceptions) and moderate levels of exposure to peers from different racial/ethnic backgrounds were both predictive of better odds that a student would improve their levels of social awareness across middle school. However, changes in student perceptions of their own sense of belonging in school were the most reliably linked to trends in social awareness. This pattern was observed consistently across intersectional demographic subgroups, suggesting that social awareness can be improved through the cultivation of more positive, caring social relationships between students and their peers and teachers.