As a result of the Post-9/11 G.I. Bill, colleges and universities across the United States are experiencing an increase in student veteran enrollment. There is limited information about student veterans making career choices, as it relates to their transition to college. This study examined what factors of career transitions (e.g., confidence, independence, support, control, and readiness) were predicted by career adaptability (e.g., control, concern, confidence, and curiosity) and occupational engagement within a developmental framework. Although career adaptabilities and occupational engagement did not predict the confidence and support aspects of career transitions, they did predict readiness. This suggests that if military service students are able to manage the idea of occupational transitions from military to college and willing to engage in specific occupational tasks, they may be ready to participate in career planning activities. Further theoretical and practical implications for researchers, clinicians, and university staff and administrations are also discussed.