The low retention rate of academically underprepared students in higher education is a concern for educators, administrators, and politicians; barriers for success in academia for the underprepared students not only include low academic skills but also noncognitive skills. The purpose of this study was to better understand the self-leadership characteristics and coping processes of academically underprepared students at a Florida community college. In addition, the study examined the relationship between self-leadership and coping; in so doing, this research builds on theoretical foundations of the emerging developmental education theory and the existing theories of coping and self-leadership. The research questions focused on how the coping processes and self-leadership characteristics differed in academically underprepared compared to academically prepared students and what association existed between general self-leadership and individual coping processes. This quantitative nonexperimental study used data collected from 1 demographic and 2 survey instruments. The statistical techniques conducted to analyze the data included Pearson correlation, MANOVA, and t test. The results of this study found no statistically significant differences between the two groups in self-leadership scores, but did find statistically significant differences in coping processes. This study also found a relationship between self-leadership and coping. This research may have significant social impact by providing a portrait of self-leadership characteristics and coping processes in a population at risk of failing to reach academic goals as well as at risk of failing to be viable contributors to family and community. This research may assist educators in developing curricula and strategies to provide support in academically underprepared students.