The purpose of this multiple case study was to examine the motivational factors behind Black students' decisions to attend either a historically Black college/university (HBCU) or a predominantly white institution (PWI) when applying to both institutional systems. The study sample included 24 total participants: 12 first-year students from an HBCU and 12 first-year students from a PWI. The primary mode of data collection was one-on-one semi-structured interviews with each participant lasting for approximately one hour. We found in the college choice process, Black students: (a) Discussed College Options with Family and School/Community Members; (b) Learned about HBCUs and PWIs through Tours, Admissions Staff, and Media, (c) Considered Family, Strategy, and Academics in Their Decision to Apply to Both; and (d) Based Final Decision on Affordability, Campus Culture, and Location. Our findings have the potential to inform how practitioners along the educational pipeline can better support Black students' college choice process.