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The prison system inherently restricts liberty in a stigmatizing and exclusionary way. This article proposes that although imprisonment restricts liberty de facto, a liberal theory of prison argues that liberty should be placed as the purpose of imprisonment and allow for a gradual reconstruction of liberty over time as part of the prison regime, especially for long-term prisoners. Imprisonment, as we argue, should be understood as a place for moral engagement with the incarcerated people’s sense of liberty and autonomy during prison and after their release. We theorize imprisonment as a source of preparation and gradual restoration incarcerated people’s physical, mental, and political liberty. When such a process is completed, the returned citizen is ready to become a full part of the civic society as a fellow autonomous citizen.