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Although low-income and minority students struggle to make informed choices about colleges that meet their needs, research suggests that school environment can play a role in supporting them in making more beneficial college choices. This paper examines evidence from qualitative interviews with low-income, African-American youth who moved from high-poverty, low-performing, segregated city schools to low-poverty, high-performing, racially-integrated suburban schools. We ask how their experiences in these schools shaped their college choices. We find that many aspired to attend four-year colleges, but encountered cultural capital barriers that led them to enroll in for-profit institutions instead. Intensive mentoring from school personnel allowed the most successful students to overcome these cultural capital barriers and enroll in colleges that served them well.