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Amid debates about race-conscious admissions and evidence of continued segregation in public K-12 schools, proponents often argue that structural racial/ethnic diversity benefits students by providing opportunities for interactions with diverse others. Using a multi-institutional, longitudinal dataset, this study examines how the specific structural environments of a student’s high school and college/university may influence their intercultural orientation after their first year of college, controlling for a host of background characteristics, attitudes, and behaviors. Results suggest that students whose transition to college involves a shift in the racial composition of their environment develop an increased intercultural orientation, even when controlling for their interactions with diverse others. However, these relationships differ based on a students’ own racial/ethnic identity.