By probing the micro-level interactions and experiences shaping students' thoughts, behaviors, and decisions during college the authors hope to generate a better picture of how individuals enact the intersection of their own agency with their given social context. Such insights may enable a more accurate and meaningful interpretation of the association between parental education, first-year GPA, and reverse transfer. Therefore, the purpose of this study is to examine the "remain or reverse transfer" decision more closely by focusing on how it occurs among graduates of Chicago Public Schools (CPS). This study reveals the multiple and complex ways in which a sample of low SES four-year college students enact choices and strategies that have an impact whether or not they remain on a four-year trajectory or experience reverse mobility. Findings demonstrate how the nuances of the pre-college goal-setting process have implications not just for access to college but also for students' trajectories through college. The importance of risk-inducing contexts and risk-management strategies emerge prominently, with the role of social capital in negotiating this process gaining central focus. As the authors see from the quantitative findings, CPS students who enroll in 4-year colleges experience reverse transfer at relatively high rates, and this pathway increases their risk of non-completion. Moving beyond the role of parental education, this analysis of qualitative data highlights the pivotal role of advocates in helping students negotiate institutional contexts that induce risk and present serious academic and financial challenges. (Contains 14 endnotes 2 tables.)