Introduction Approximately 200,000 U.S. military members leave the armed services each year. Since its inception in 1991, the U.S. military's Transition Assistance Program (TAP) has sought to help prepare these military members for their shift to civilian life. Despite recent modifications, TAP continues to largely ignore the full range of challenges and life changes faced by transitioning military members as they leave the service. TAP principally focuses on preparing transitioning military members for employment or education after their service along with helping them understand and apply for a broad range of available veteran's benefits (Congressional Research Service, 2018). While many separating military members successfully adapt to civilian life, 40 to 75% describe some difficulties managing this major adjustment (Castro & Kintzle, 2017; Zoli, Maury, & Fay, 2015). These difficulties include problems adjusting to educational or work settings, substance abuse, homelessness, financial mismanagement issues, confrontations with the criminal justice system, family problems, and military-related Post-Traumatic Stress Disorder (PTSD) responses (