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A higher education degree has become an increasingly important determinant of occupational success and earnings. Social scientific interest and analyses of student enrollment, engagement and completion has intensified over the prior decade. Though an emerging body of literature has begun exploring the experiences of first-generation students, most accounts to date provide one-time cross-sectional snapshots rather than longitudinal insights. Many tend to be derived from samples of students attending private institutions where first-generation student are unlikely to enroll. To understand why first-generation status matters in creating or blocking opportunities for upward mobility, this project interviewed 66 first-generation students each year for four years. Ten students who dropped out will be subsequently interviewed, and the two groups compared.