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Public, private, and non-profit criminal justice professionals form the fabric of reentry today. Their work mediates the link between financial resources and the outcomes of ex-offenders. In this paper I examine how criminal justice practitioners understand and construct the post-imprisonment environment. Using 25 interviews with practitioners, this work demonstrates the importance of employment, housing, and family networks for a positive reentry experience. Yet, these practitioners have more to say about reentry than what works or doesn’t. Their work is also informed by larger American ideas regarding opportunity, fairness, and equality. I illustrate how criminal justice professionals grapple with cultural understandings of opportunity on the one hand, and the day-to-day structural realities of the marginalized population they serve on the other. In a society where the developing language of reentry is one of second chances, I also find that those administering various reentry services are actively engaged in local processes of cultural change. That is, as reentry workers adapt to meso- and macro- level reentry transformations, they are re-hashing the micro reentry terrain through discursive and interactional practices.