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Drawing from two unrelated lawsuits that reached the Casa da Suplicação, Brazil’s highest court of appeals, between 1808 and 1831, this paper discusses the upbringing of illegitimate girls born to enslaved mothers and enslaver fathers within plantation households. In each of the two cases, the girl’s widowed, white paternal grandmother freed the girl after her father’s death. Acting as the matriarch of her respective extended family, each grandmother raised her formerly enslaved granddaughter to take an elevated place within the household. When each of the two matriarchs died, her surviving children (the girl’s aunts and uncles) sought to sever the familial relationship and re-enslave the girl, denying that their deceased brother was her father and accusing her of ingratitude for attempting to claim an inheritance. The remarkably similar plots in these two unrelated stories illustrate the range of social and familial norms that structured biological relationships between enslavers and the women and children they enslaved at the end of the colonial period. The stories allow a close look at the emotional violence suffered by freed children whose status and freedom depended on constant displays of dependence and gratitude to their white relatives. Their adjudication illustrates the ways the Portuguese courts understood the multi-layered “customs” that structured familial and labor relationships within the colonial plantation household.