To reflect academic challenges and enrollment patterns of today's freshmen, this study measures the impact of high school preparation, first-year academic performance, multi-institution enrollment, and financial aid support on second-year persistence. Using multi-year cohorts at a public research university, results confirm the importance of including first-year math experience, math intensity of the declared major, simultaneous enrollment at another college/university, and second-year financial aid offers when measuring freshmen retention. The positive impact of a large-scale, state-funded scholarship program in widening access to college must be balanced against findings that show academic performance and readiness to take on and pass first-year math to be more important than aid in explaining freshmen dropout and transfer-out during both first and second semesters. Middle-income students with greater levels of unmet need face an elevated departure risk, while academically well-prepared freshmen with unmet need are more likely to transfer to other institutions.