As educators and service providers in urban schools encourage student college going at higher rates than ever, policy and practice on school improvement discourses would benefit from incorporating students' perspectives underlying family-based, "college-going dilemmas" that frame their college preparation. This qualitative article features the voiced experiences of 11th-grade adolescent boys, one Black and one Latino, from one school, as they grapple with both "internal dilemmas" (e.g., fear of changing and being distanced from their family) and "external dilemmas" (e.g., their expected familial commitments) inherent in their college access, success, and graduation. Using a conceptual framework that considers the social, cognitive, and institutional factors influencing their college preparation, this article focuses on social factors and advocates for institutional practices that better meet student needs.