To date, most studies exploring the effects of student loans on college enrollment have focused on persistence and completion, although increasing student mobility between institutions elevates the importance of considering a wider range of enrollment outcomes, specifically student transfer. Nearly 40% of students begin at a public or private non-profit 4-year college transfer within 6 years (Shapiro et al. in Transfer and mobility: A national view of student movement in postsecondary institutions, Fall 2011 Cohort (Signature Report No. 15), National Student Clearinghouse Research Center, Herndon, VA, 2018), yet we know little about the relationship between student finances and the decision to transfer. Using data from the Beginning Postsecondary Student Survey (BPS), a longstanding National Center for Education Statistics (NCES) dataset, from two nationally representative cohorts of students entering 4-year institutions in 2004 and 2012, we examined patterns of student borrowing and college students’ transfer over time. Additionally, via marginal mean weighting through stratification (MMW-S) methods, we identified whether student borrowing behavior affects the likelihood of student transfer over the last 2 decades. We found that students in the 2012 cohort had a higher proportion of high-level loans across all outcomes, including transfer, retention, and dropout, compared to the 2004 cohort. In both cohorts, transfer students were the most likely to have borrowed at the high loan level. Among dependent students enrolled at 4-year institutions, low-levels of federal loan borrowing in the first year are positively associated with transfer relative to retention, whereas mid-levels of borrowing are positively associated with transfer relative to dropout, consistent across both cohorts. These findings shed important light on how student loans may differentially influence the decision to transfer versus the decision to stay or to drop out. As policymakers consider the wide-scale adoption of transfer pathways across institutions, understanding the relationship between student loans and student transfer is all the more critical.