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This article offers a microhistory of the trajectories toward freedom of three generations of Afrodescendant women in a single household in early-nineteenth-century Buenos Aires (Argentina) during the gradual abolition of slavery. Their stories demonstrate the precariousness of freedom in a society often considered peripheral to geographies of American slavery and celebrated for its purportedly exceptional racelessness and class dynamism. But they also illuminate unremarked changes in the nature of slavery in postrevolutionary Buenos Aires and the spaces for maneuver leveraged by Afrodescendant women against a backdrop of political and economic transformation. The article pays special attention to the youngest of these individuals: Cayetana Warnes, afreeborn girl nonetheless repeatedly inscribed in notarial and probate records as a "liberta." Cayetana's story provides the basis for a new examination of "liberto/a," the juridical category in-between slavery and freedom created by the 1813 Free Womb Law that conditionally freed the children of slave mothers after a term of service to their mother's master. Though unusual and indeed illegal, the process by which the freeborn Cayetana became a fictional "liberta"—combining dynamics of contracted and coerced labor, spiritual kinship, gender, minority, tutelary servitude, and inheritance—exposes a range of more ordinary practices through which the racialized and coercive relations of slavery shaped Argentina's emerging free labor regime, and vice versa. In these ambiguous spaces, Cayetana's foremothers used their positions inside and outside the household to shape their own freedom and to negotiate, not disadvantageously, the terms of unfree labor across the generations.