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This study examines the role that British convict transportation and penal servitude in America played in the early history of humanitarianism. During the eighteenth century Britons' and Americans' ideas about moral obligations and suffering changed drastically toward traditionally detested people, including transported convicts, enslaved Africans, sailors, and the poor. Historians have made it clear that people in the eighteenth century created unprecedented ways to understand the human condition, and studying coerced labor of all kinds tells scholars more about how unfreedom shaped the language, ethics, and practices of the early stages of humanitarianism. In the eighteenth century British courts banished over 50,000 convicted men, women, and children to the American colonies, many of whom were sold as convict servants. This study argues that emerging ideas of punishment, morality, and unfreedom evoked by convict labor created new moral responsibilities, widened the plane of sympathies, and inspired novel denunciations of suffering in eighteenth century Anglo-American culture. Institutional banishment and convict servitude had unintentional consequences for both Britain and America, and moralists and elites constructed a new discursive environment that raised complex questions and generated new debates about labor, coercion, and cruelty in the Age of Enlightenment and Revolution.