Abstract: Military experience alone is no longer enough to replace a college degree for many civilian jobs, leaving nearly 15% of transitioning veterans at a disadvantage without higher education credentials. This study explored how active-duty Marines decide whether to pursue postsecondary education and assessed the role of the voluntary education (VolED) program in this process. Using a qualitative case study design, data were collected through interviews with 10 Marine veterans, ranked E-1–E-5, who transitioned within 1–2 years of the study. Results showed motivations for pursuing education included the desire to upskill, attract employers, and follow personal passions, while barriers included lack of support, resources, time, and financial challenges. The findings suggest the VolED program could improve by increasing access to information and educational pathways before military separation. This research highlights strategies to better support Marines transitioning to civilian life and offers insights for further exploration of factors influencing their educational decisions.