Background/Context One of the most critical functions of a well-integrated school is the development of “culturally flexible” students who, over the course of their social development, effectively navigate diverse social environs such as the workplace, communities, and neighborhoods. Most studies, albeit with some exceptions, have investigated the impact of desegregation on short- and long-term gains in achievement and attainment, as opposed to its impact on intergroup relations. Mixed-race schools are vital not only for bolstering achievement outcomes of previously disadvantaged students but also for promoting social cohesion in a diverse society. Purpose/Objective/Research Question/Focus of Study Specifically, this article examines the difference in cultural flexibility between black and white students enrolled in schools with different racial and ethnic compositions. Cultural flexibility is defined as the propensity to value and move across different cultural and social peer groups and environments. Furthermore, this article provides some insight into how students in different mixed-race and desegregated educational contexts experience their school's social organization and cultural environments, which influence their interactions and academic behaviors. Setting The study was conducted over a 6-month period in four high schools: a majority-minority school and a majority-white school located in a northeastern city, and a majority-minority school and a majority-white school located in a southern city. Research Design Survey data were gathered from a randomly stratified sample of 471 Black and White students attending. In addition, ethnographic notes from weeks of school observations and transcribed interview data from 57 group interviews conducted in the four schools with students in Grades 9–12 complemented the survey research. Data Collection and Analysis Findings reveal significant associations among self-esteem, academic and extracurricular placement, and cultural flexibility for black students. Also, black students in majority-minority schools scored significantly higher on the cultural flexibility scale than those in majority-white schools. Among white students, regional location and academic placement showed statistically significant associations with cultural flexibility. The ethnographic and interview data further explicate why these patterns occurred and illuminate how certain school contextual factors are likely linked to students’ cultural flexibility. Overall, this study's findings highlight some connections between student and school behaviors as they pertain to both students’ and educators’ willingness and ability to realize the visions of racial and ethnic integration wholly.