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The experience of imprisonment conditions the expectations of those who have been penalized. Not only will there be the stigma of a penal sanction after release, but prisons constrain the prisoner’s self-directed (or agentic) action while inside. This paper considers the results of research into the impact of context on disposition, and thus on behavior, from the philosophers who study forms of implicit bias. Many varieties of post-prison programming are directive and cultivate compliance with a set of rules and conditions. The research into context and agency suggests that such “thin” forms of intentional action may be compromised when the former prisoner encounters challenges. The designs of various types of post-prison programs are analyzed in terms of the support they provide for aspiration and agentic action.