This panel addresses the ways in which early modern prisoners of war were set to work, how contemporary legal and ethical concepts prescribed the employment or enslavement of prisoners, and how officials and masters legitimized their emergent practices as they went along. With analyses of three important moments in which transitioning governments struggled to extract labor from captives, the panelists contribute to the history of economic life, the history of war and society, and the history of slavery and servitude. Elisa Frühauf Garcia shows how the mid-sixteenth-century Portuguese manipulated categories of race and status in order to access the native women in São Vicente, Brazil. They needed these women as alliance brokers, but increasingly placed them under the label of captives, who could become bonded and commodified laborers. Moving from a site of new encounters and colonization to one of established commercial and territorial rivalries, Sonia Tycko demonstrates the legal ambiguity and practical challenges in mid-seventeenth-century employment of Scottish and Dutch prisoners of war in the English fenlands. More than a century later, the Revolutionary American forces extemporized when faced with similar issues with captured British soldiers. T. Cole Jones considers how the first American prisoner of war policy was built based on the experiences of setting British captives to labor in Connecticut farms in the first years of the American Revolutionary War. These papers will spark a conversation with the audience about the role of labor in prisoners’ material experiences, the history of categorization and legitimization of work in captivity, and how prisoners can reveal anew the relationship between various warring governments and the commercial activities of their subjects, allies, and enemies.