<p>Higher education can pose significant challenges for students, including the need to adapt to new academic environments and social dynamics. These challenges may affect their well-being and increase the likelihood of dropping out. This study explores social support as a mediating mechanism through which well-being influences dropout intention among higher education students—that is, higher levels of well-being may lead to more positive perceptions of social support, which may in turn contribute to a lower dropout intention. In addition, this study explores whether these relationships vary depending on moderating variables such as whether the course attended was the student’s first choice, cycle of studies, student-worker status, having dependents, and being a displaced student. A total of 1404 Portuguese university students participated in the study by completing questionnaires related to socio-economic variables, emotional well-being, satisfaction with social support, and the dropout intention. The results suggest the following: (1) social support from family did not mediate the relationship between well-being and dropout intention; (2) social support from social activities and friends partially mediated the relationship between well-being and dropout intention; and (3) social support from intimacy fully mediated the relationship between well-being and dropout intention; and (4) the conditional indirect effect suggests that the mediation of social support in the relationship between well-being and dropout intention is stronger for students without dependents and non-displaced students. It is essential to implement interventions on higher education campuses that are personalised and that foster the most effective sources of support, while respecting the specificities of students at risk of dropping out.</p>