The transition to college is one of the first major transitions in life for many individuals and can represent a susceptible time for mental health issues. Male students are particularly susceptible with less mental health support surrounding them in general. It is critical to understand factors that impact adjustment in college students as they can represent target interventions for practitioners to help foster personal-emotional adjustment. The present study was undertaken to fill data gaps in the research on emotional adjustment among male college students. This study utilizes multi-level data to understand the dynamic process of emotional adjustment in college to see if factors affecting adjustment differ over time. This study also includes multi-level risk and protective factors, from individual, to interpersonal, to institutional. Including institutional-level factors may allow for a greater understanding of how the college itself may impact emotional adjustment among students. We observed that emotional adjustment was largely stable over the first two years of college. While some of the factors investigated had statistically significant associations with emotional adjustment, we largely found small magnitudes of effect indicating that there are limited practical implications in what we observed. Future research directed at understanding the interplay between factors at various levels is warranted.