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Educational programming often supports desistance for individuals involved in gangs. However, there is an empirical gap in understanding how and why former or inactive gang members pursue higher education and the reasons behind choosing specific fields of study. This paper highlights initial exposure to postsecondary education and how these individuals select a field of study, drawing from life history interviews with 30 former or inactive gang members who graduated from two- and four-year colleges and universities. For the participants in this study, on average, they were gang-involved for more than 10 years. Special attention will be given to individual and structural factors, including college personnel and specific programs that support vulnerable student populations and promote persistence in college to attain degrees.