Many attempts have been made to justify punishment by invoking the moral autonomy and dignity of those who are subject to it. Yet the most refined of these attempts have been informed by an awareness of paradox. For the practice of punishment, so closely linked to concepts of individual freedom, tends to degrade those subjected to it. And as a form of state action predicated on claims of moral or social solidarity, it often prevents inquiry into the ways that individual culpability coexists within broader political forms of responsibility. This essay explores the ways in which college in prison programs like the Bard Prison Initiative may intervene in this paradox of punishment.