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While policy-makers and scholars often measure the success of prison education programs by quantitative outcomes such as recidivism and post-release employment opportunities, there is a gap in the literature with regard to how these programs shape a prisoner’s sense of agency, self-authorship, and identity. For the 159,000 people serving life sentences in the United States, we need a new way of conceptualizing the purpose of education that opens up our understanding of what the purpose of education in prison is. Using portraiture, I explore how five men serving life sentences in a Massachusetts state prison make meaning of education in a way that moves beyond instrumentalism and vocation, and instead toward cognitive liberation and a reclamation of humanity.