Not only is achieving a four-year degree beneficial for individual students, keeping students enrolled until graduation is beneficial for the institution as well. Decreases in state funding of higher education as well as the increasing number of states having adopted some kind of performance based funding (PFB) model, have resulted in many institutions relying on enrollment and retention for fiscal purposes. Because attrition rates are highest during students’ first year of college, it is important for institutions to find ways of engaging first-time, full-time freshmen in educationally purposeful activities early in their college career to aid in retention efforts. Early-enrollment instruments and the use of data analytics can be useful in identifying student risk factors that may lead to their not returning to college for their second year. Institutions can utilize early-enrollment instruments not only to identify risk factors, but also to create a holistic plan for college success during their first year. This study investigated first-time, full-time freshmen participating in a special admission program at a large, research institution in the South, exploring the influence of background characteristics on student anticipated engagement prior to enrollment, and actual engagement in the first semester, and how background characteristics, anticipated engagement, and actual advising and Student Life engagement predict first-term GPA, first-term credits earned, and continued enrollment in the next consecutive term. Findings indicate significant differences in anticipated and actual engagement by background characteristics, and the background characteristics, and anticipated and actual engagement can predict student success measures such as GPA and credits earned.