Objective: For many students, community college is a convenient first step toward a bachelor's degree. Yet, although more than 80% of those who enroll in community colleges intend to transfer to a 4-year institution, fewer than 35% do so within 6 years. Quantitative data reveal the presence of a transfer gap and there is extensive research on college choice for high school students, but little qualitative research has been done to examine the transfer process for community college students to identify what drives their decisions. Method: In this article, we draw on interviews with 58 community college students in Texas to examine how they made transfer decisions. Results: We find that their decision-making and transfer pathways were complex and nonlinear in ways that were particular to the uncertainty of the community college context. For a subset of students, we identify minor hurdles that could derail their decision-making, lengthen their timelines to transfer, or lead to a failure to transfer. Contribution: By illuminating student pathways to transfer using qualitative research, our work identifies potential areas where policy and practice could strengthen transfer to improve student outcomes.