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Research has found support for the perpetuation hypothesis, which predicts that the racial contexts that youth grow up in direct them into analogous ones in their futures. However, there is a lack qualitative research that examines how high school racial context influences the racial composition of the colleges students attend. Drawing upon interviews and observational data with 48 Black students at two racially and socioeconomically diverse high schools, I examine if the perpetuation hypothesis predicts students’ college preferences and how this process works. My data indicates that although many students’ college decisions would seem to provide support for the perpetuation hypothesis, their reasoning complicates it. I argue that the schools’ conflicting messages contributed to students' complicated college diversity preferences.