We studied the effects of academic performance, motivation, and social connectedness on third-year retention, transfer, and dropout behavior. To accommodate the three outcome categories and nesting of data within institutions, we fit a hierarchical multinomial logistic regression path model with first-year academic performance as a mediating effect. Our sample included 6,872 students representing 23 four-year universities and colleges. This work expands the current state of persistence research by (1) considering the effects of motivation and social connectedness on college persistence beyond the first year of college, (2) testing whether the effects of motivation and social connectedness on third-year retention and transfer are direct, indirect, or both, and (3) testing whether the effects of academic performance, motivation, and social connectedness are different for retention and transfer. We found that academic performance has large effects on likelihood of retention and transfer; academic self-discipline, pre-college academic performance, and pre-college educational development have indirect effects on retention and transfer; and college commitment and social connectedness have direct effects on retention. Academic self-discipline led to greater first-year academic performance, which suppressed its effect on retention and transfer. Practical and theoretical implications of these findings and directions for future research are discussed.