Most military veterans who reside in a central U.S. city have not entirely used their Montgomery G.I. Bill (MGIB) education benefits to advance their careers. There is limited research on veterans' views of the effect of certain barriers, identified from prior research, on academic persistence. The problem of the lack of specific information about the barriers that prevent military veterans residing in a central U.S. city, from fully using the benefits of the MGIB, was addressed in this study. Clark and Caffarella's transition theory was used in this case study to explore the perceptions of eight military veterans on reason they dropped out of college or never used the MGIB to attend college. The research questions focused on military veterans' views of strengths and weaknesses of the G.I. Bill while they were in active duty, at the time they made the decision to not use it or respectively how the U.S. Department of Veterans Affairs processed their eligibility. Thematic analysis findings from the data collected with face-to-face semi-structured interviews revealed five themes that described military veterans' views of the barriers they faced during their duty from their supervisors, perceptions of the MGIB during active duty, applying for college, having a family prevented the use of the benefits, expired MGIB benefits, and having a job that prevented the use of the MGIB. The resulting project consisted of a white paper that proposed recommendations of how military veterans could successfully improve their academic progress towards earning a college degree. The project contributes to positive social change by informing future military recruits, active-duty military personnel, military veterans, and military veteran organizations of potential strategies to help military veterans effectively use the MGIB benefits to earn a college degree.