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There is an equity dilemma plaguing the U.S. when considering American incarceration by gender and race/ethnicity. There is a radicalized criminal profiling of males of color that corresponds with disparate sentencing and imprisonment. While African Americans make up 13% of the U.S. population, yet African American males comprise 17% of the prison population. The rate of African American male incarceration has tripled over the last 30 years. Educational attainment and incarceration have an inverse relationship as one-third of African American males imprisoned do not have a high school diploma or GED. Hence, more efforts to steer African American males from cellblocks into classrooms are needed. Historically, the community college have prided themselves on providing access to postsecondary education for students who otherwise have no other college option. This chapter explores the school to prison pipeline, racial disparities that exist across the educational pipeline, and how the community college has played a vital role in postsecondary access for African American males via prison education programs. The presentation highlights best practices, policy recommendations, and shares the experiences of African American males that participated in prison education programming and how they successfully transitioned following release.