This study addresses the enslaved and free people of African descent in colonial Oaxaca between the 1650s and 1820s. The presence of African captives and their descendants in Oaxaca has long been silenced in the historiography of the Valley of Oaxaca, Latin America, and the broader African Diaspora. By cross-referencing notarial, judicial, and Inquisition records with censuses and marriage registers, I reconstruct the populations of free-coloreds and slaves in Antequera and its surrounding regions from 1650 to 1829. My notarial investigation involves an analysis of bills of sale, manumission letters, wills, and property inventories produced between 1650 and 1740. Likewise, I examine civil and criminal cases and Inquisition records to reveal the everyday lives and cross-cultural contact between African descent people and other ethnic groups. Based on these records, I find that enslaved people arrived in Oaxaca from areas across the Atlantic and Pacific worlds, including Africa, Europe, Asia, and the Americas. Free-persons and slaves met the labor demands of wealthy Spaniards in Oaxaca, and they worked in the city of Antequera as skilled and unskilled laborers, artisans, and professionals during the colonial period. By the eighteenth century, Antequera became a diverse society comprised of multiple ethnic groups, including Spaniards, Africans, Indians, and mestizos. In the early eighteenth century, the population in the Valley of Oaxaca grew because the indigenous populations had recovered from a series of epidemics during the Conquest. Likewise, the mixed-race populations increased significantly due to a rise in mestizaje. Thus, these inter-ethnic unions contributed to the diversity of this colonial society. By the late colonial period, the definitions of social status changed to include status markers based on race, occupation, property ownership, and access to power. Free coloreds made up the middle and lower classes of this social hierarchy, and they often lived and worked alongside other casta groups who belonged to the same social classes. Although the Spanish colonial state implemented several measures to control casta groups, free and enslaved people used multiple strategies to contest elite expectations of race, forge ties with ethnic others, and construct their own experiences and identities in Oaxaca.