This article examines postmortem inventories and notarial records from Brazilian slaveholders in southern Brazil in the nineteenth century. By discussing selected cases in detail, it investigates the relationship between “precarious masters” (especially the poor and/or disabled, widows without family, and single elderly slaveholding women and men) and their slaves and former slaves to whom they bequeathed, in their testaments and final wills, manumission and property. The article reads these documents as intergenerational contractual arrangements that connected the masters’ expectations for care in illness and old age with the slaves’ and former slaves’ expectations for compensation for their work and dedication. Following these uneven relationships of interdependence and exploitation as they developed over time, the article suggests a reassessment of the role of paternalism in Brazil during the country’s final century of slavery. More than a tool to enforce relations of domination, paternalism articulated with the dynamics of vulnerability and interdependency as they changed over the life courses of both enslaved people and slave owners. This article shows how human aging became a terrain of negotiation and struggle as Brazilian slave society transformed throughout the nineteenth century.