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Using data from a large-scale adolescent survey of students of color and students from low-income households enrolled in advanced high school courses (N = 61,403), the current study examined the links between school belonging, belonging certainty, and student engagement. Supportive, inclusive school cultures where belonging and engagement are foundational are important for increasing equitable enrollment in advanced high school courses and preparing students for college and beyond. Results demonstrated that a multidimensional assessment of belonging-rich school environment (i.e., classroom community, expectations, feedback, and assessments conversations about race, culturally relevant curriculum, culturally relevant teaching constructs) significantly predicted student-reported engagement. Mediation analyses revealed that belonging certainty did mediate the relation between these belonging constructs and engagement.