Objective: The current study examined predictors of well-being, including quality of life and academic engagement, in a sample of student service members and veteran college students. Methods: Eighty-seven student service members/veterans (SSM/V) completed an online survey containing questions about post-deployment social support, emotion regulation skills, psychological distress, academic engagement, quality of life, and demographics. Participants were recruited from September 2012 through May 2014. Results: Results provided partial support for the proposed bi-directional mediational relations between post-deployment social support and emotion regulation predicting to quality of life and academic engagement. Path models indicated that both post-deployment social support and emotion regulation skills partially mediated the relation with quality of life while accounting for the effect of psychological distress, and that emotion regulation skills fully mediated the relation between social support and academic engagement. Conclusions: These findings suggest that both social support and emotion regulation skills may be useful targets for health promotion and intervention efforts for this population. Limitations and clinical implications for the development of on-campus SSM/V focused health promotion services are discussed.