The transition from the regimented environment of military service to a less structured college lifestyle can be stressful for student veterans with and without disabilities, which highlights the importance of exploring protective person-environmental contextual factors that can help student veterans with and without disabilities manage their stress effectively, leading to enhanced well-being. The purpose of this cross-sectional correlational design study was to examine the role of positive person-environment contextual factors, including hope, resilience, core self-evaluations, and social support, to reduce the influence of perceived stress on the subjective well-being (SWB) of student veterans with and without disabilities. The sample included 205 student veterans (71.7% males; 80.5% White; Mage = 29.32; 39% with service-connected disability). Findings suggested that core self-evaluations and social support partially mediated the relationship between perceived stress and SWB in student veterans with and without disabilities. Implications for clinicians, university counselors, and university staff are also discussed.