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This comparative case study documents the structural and normative aspects of the college choice process at two majority-Black neighborhood high schools within a highly racially and economically segregated major Midwestern school district where many Black students who aspire to attend college fail to enroll. Over the course of five months I interviewed school personnel, seniors who aspired to attend college, and conducted observations to examine the impact of socioeconomic composition on the college choice process and student decision-making. The study found that school personnel organized the college choice process in response to perceptions of students’ social class resulting in a highly structured, stratified, and constrained process for students attending the socioeconomically isolated high school.