This qualitative study explored the high school to college transition experiences of ten successful first-generation college students (FGCS). Participants were college seniors at an historically black university in the United States. A generic qualitative research design was used, including in-depth, semi-structured interviews to collect and analyze data. Participants reported that the transition experience led to confusion with academic and financial procedures, various emotions including anxiety and fear, the realization that they had deficits in academic skills, and the receipt of support from family members and others. Cultural and social capital appeared to play key roles in their success. Student affairs professionals are encouraged to explore targeted, individualized strategies that meet the needs of FGCS as they transition to college.