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The Second Chance Act of 2007 is a few years shy of 20 years old, and the aspirations of this legislature are even further from realization. The reentry movement, which began a few years before the passage of federal legislature, has stalled because of the organizational quagmire—who owns the reentry process, and is reentry part of community supervision? Initially, reentry was centered on institutional corrections with the notion that reentry begins at the time of intake to prison. This paper will examine why reentry has not come to fruition by exploring the barriers from the lens of institutional corrections, community corrections, societal perspectives, and individuals involved in the reentry process. The complex issues of the culture of control, stigma, and racism affect each perspective and how the barriers are manifested. These perspectives are confounded by reentry needing extra-legal organizations like housing, employment, child welfare, substance use treatment, mental health treatment and/or other non-legal entities, and yet structural issues (i.e., organizational mission/goals, resources, prioritization, etc.) often prevent such organizations from being part of the reentry process. This paper will outline how reintegration can become reentry with further attention to the socio-political issues that affect reform.