Drawing on thirty freedom suits from nineteenth-century eastern Cuba, this article explores how some slaves redefined slaveholders' oral promises of manumissions by grace from philanthropic acts into contracts providing a deferred wage payout. Manumissions by grace tended to reward affective labor (loyalty, affection) and to be granted to domestic slaves. Across Cuba, as in other slave societies of Spanish America, through self-purchase, slaves made sustained efforts to monetize the labor that they did by virtue of their ascribed status. The monetization of affective work stands out amongst such efforts. Freedom litigants involved in conflicts over manumissions by grace emphasized the market logics in domestic slavery, revealing that slavery was a fundamentally economic institution even in such instances where it appeared to be intertwined with kinship and domesticity. Through this move, they challenged the assumption that slaves toiled loyally for masters out of a natural commitment to an unchanging master-slave hierarchy. By the 1880s, through court litigation and extra-judicial violence, slave litigants and insurgents would turn oral promises of manumission by grace into a blueprint for general emancipation. Through their legal actions, enslaved people, especially women, revealed the significance and transactional nature of care work, a notion familiar to us today.