Little is known about the academic and career decision‐making process for college students with undocumented status. This study used a multiple case study approach to explore how academic and work‐related decisions were made for 2 college students with undocumented citizenship status. Participants responded to a series of questions about their academic and career development. Data collected from these interviews were analyzed by a research team. After cross‐case analysis, 6 themes emerged: (a) barriers; (b) emotional impact; (c) resiliency, supports, and coping; (d) discrimination; (e) familial and cultural influences; and (f) academic, work, and career factors. Findings suggest that counseling professionals should attend to systemic, academic, and work‐related barriers that directly affect the educational and career decisions of students with undocumented citizenship status. Future research could expand on the present study by further exploring systemic and contextual factors that influence how undocumented students make academic and career choices using varied qualitative and quantitative methodologies.