This article addresses the robust market in “Indian medicine” that flourished in the nineteenth century—partly due to the influence of urbanization, industrialization, and new technologies of print—and the specific roles that Indian doctresses played in that phenomenon. Indian doctresses in the United States operated at the intersection of cultural values and beliefs regarding womanhood, medicine, and American Indians. Not all of these women were of Native ancestry, but they all mobilized widespread ideas about Native peoples while seeking entrepreneurial success as healers. Using print culture, the author analyzes strategies employed by women who worked as Indian doctresses and patterns of reactions to their efforts. By combining profiles of women who worked as Indian doctresses with popular but not always positive representations of the type, the article offers a kind of composite biography of an occupation. Women from a wide variety of backgrounds fused caregiving skills with popular assumptions—particularly those involving “indigenous anti-modernity”—to make a living. In this way, Indian doctresses also became useful symbolic figures upon whom changing conceptions of race, gender, and class could be projected and debated. The author thus aims to shed new light not only on histories of American medicine but also on the labors of American women and the business of Indian representation during the nineteenth century.