This study examines the dispositions and experiences of support of college students associated with unexpected pathways toward college graduation. The final sample was drawn from a national sample of 3,998 youths who participated in a longitudinal project. Using the k-nearest neighbors' algorithm, we created four groups based on the Québec High School Average and the College Graduation status four years after admission (Unexpected Graduates; Expected Dropouts; Unexpected Dropouts; Expected Graduates). Compared to ED, UG showed lower aggressive behaviors and attentional problems and higher participation in institutional or targeted support measures in college. They were also more likely to have attended a private high school. Compared to EG, UD showed lower academic behaviors and motivation, lower perceptions of teaching quality and support, and lower economic capital and support from family. They were also more likely to enrol in a technical college program and less likely to have attended a private high school.