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This study examined school engagement and future expectations in a culturally diverse sample of high school students. The analyses examined how students’ future expectations were related to behavioral and affective engagement as well as to perceptions of classroom climate. Thus engagement and perceived classroom climate served as predictors of students’ beliefs about the future. Results revealed that perceived climate and measures of student engagement were indeed related to future expectations, and this relationship was moderated by ethnicity. Overall, our findings speak to the powerful impact of relationships for sustaining student engagement, and we draw implications for schools about the broad variability that can be subsumed under monolithic racial labels.