Within a decade following World War II, more than two million veterans attended college through the use of the GI Bill, with an additional almost 5.5 million taking advantage of vocational training (Mettler, 2005). Now, over fifty years later, “Only one in ten veterans using GI Bill benefits enrolls in institutions with graduation rates above 70 percent, while approximately one in three veterans using GI Bill benefits attends a for-profit institution” (Bond Hill et. al, 2019). During that time, the armed forces has consistently had Black adults enlist at the rate comparable if not disproportionate to their population percentage, despite recent down trends in enlistment (Segal & Segal, 2005). Through aforementioned opportunities like the GI Bill and Yellow Ribbon Funds, this dissertation aims to examine how Black youth and veterans are able or unable to reach their educational goals based on legislation, resources provided by the military, and anti-Blackness. Previous research studying the effectiveness of the GI Bill, recruitment efforts, and the integration of the armed forces into K-12/ post-secondary education, guides my methodology. As such, I utilize a mixed methods approach to collect oral histories as well as Geographical Information Systems (GIS) open source data on college and university endowment, racial demographics at institutions of higher education, the locations of military bases and racialized violence, and related statistics to measure engagement between Black communities and the armed forces through an educational pipeline. The ultimate goal of this research project is to inform how educators, policymakers, Black veterans and youth recognize and respond to the influence of the armed forces in education to make choices that are well suited for future generations and not just those currently enlisted.