Demographic shifts in the United States have resulted in similar demographic shifts between K-12 teachers and their students, resulting in important implications for the educational outcomes of traditionally marginalized students and educators' cultural awareness required in teaching diverse classrooms. Using data from the Three-City Teacher Study, this study examined students' (N = 207; 55 % female; 52 % non-Hispanic Black, 48 % non-White Hispanic; mean age = 16.70 years, SD = 1.67) and teachers' (N = 202; 71.5 % female; 64.3 % white; mean years of experience = 13.80 years, SD = 10.83) agreement on the potential educational attainment of the student. Specifically, we explored the probability that teachers had lower, matched, or higher perceptions of educational attainment compared to their low-income Black and Hispanic students' perceptions of attainment while accounting for teachers' and students' reports of school connectedness, teachers' cultural awareness, and moderating effects of students' race. Results from multinomial logistic regressions found that teachers were more likely to have lower perceptions of educational attainment for Hispanic students compared to Black students. Teachers were also more likely to have lower perceptions when they perceived students to have low school connectedness. For Black students, teachers' cultural awareness attenuated this association; that is, teachers were more likely to have higher perceptions of educational attainment for Black students when they reported higher cultural awareness. The reverse was true for Hispanic students. These results enhance our understanding of how teacher and student perceptions shape expectations of educational attainment with implications for teacher education and professional development domestically and internationally.