One in three students suffers from at least one common mental disorder highlighting the high prevalence of health issues in higher education. At the same time, every third student drops out of university without achieving their degrees. Nevertheless, connections between health and students' dropout behavior have hardly been investigated. Grounding on value-expectation theory, this article argues that the students' health-related quality of life (HRQoL) alters the impact of their self-assessed success probability in graduating on their dropout intentions. To examine the research question, data from the LAST project, which surveyed a German undergraduate student population over a period of four semesters (N = 7,169), were used applying fixed effects regressions, and interaction effects. Analyses uncover that the students' mental health status is in fact linked to their intentions to drop out of university. Furthermore, an interaction effect of mental HRQoL and success probability could be confirmed. The findings suggest that universities should adopt better health promotion policies that bring together both individual health needs and higher education's interest in successful graduates.