Few qualitative studies consider how high school experiences affect readiness for diversity engagement in college. Using data from an ethnographic case study, three central trends (student experiences within homogeneous high schools, racial divisions within diverse high schools, and students who attended diverse high schools but had little engagement with that diversity) illustrate how students can enter college without meaningful engagement around diversity, even when they attend racially diverse high schools. Findings underscore the essentialness of critically engaging students around issues of race and diversity during the college years, given the general lack of meaningful engagement prior to college.