With the number of transfer students increasing and graduation still an elusive goal, the researchers conducted four focus groups and four individual interviews with transfer students attending universities in the Chicago and Dallas-Fort Worth area to better understand and explore the factors that influenced their college choice decisions at their first and subsequent institutions. The specific research questions were: (a) When, why, and how do transfer students select their postsecondary institutions? (b) How do students who have transferred more than once describe their decision-making process and has it changed from their initial college choice decision? The study found many students did not pursue planned, linear pathways to transfer. Rather, they often made spontaneous decisions affected by a range of personal as well as academic issues. The article includes implications for student affairs professionals and high school counselors to facilitate the college choice process.