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This longitudinal qualitative multi-site case study presents data from eight high school students and their guidance counselors attending two high schools in a mid-sized urban school district. Organizational habitus is used to explore how school context shaped students’ college aspirations and college choice from grades 9-12. Findings suggest the school’s organizational structure, including the mission, available resources devoted to college preparation, support for college advising, and the interaction between guidance counselors and students influenced whether students participated in the college-going process and also where they chose to enroll. Implications for this research suggest the need to illuminate organizational barriers in the college choice process and develop polices which are aimed at addressing the schools’ role in reproducing social inequality.