Working closely with a detailed 1582 register of the free Afro-Peruvian population of Cusco, Peru, this article explores how the strategic representations of individual registrants reflect the intersectional impact of unfree labor practices and increasing racial marginalization in the early colonial Andes. The growing population of free Afro-Peruvian men and women navigated practices and policies that promoted racial inequalities and coerced labor based on race, class, and gender. The 1582 registry reflects municipal attempts to subject Cusco’s free Afro-Peruvians to ordinances that acknowledged the relative independence of skilled workers (oficiales), while requiring others to reside and serve in the homes of Spanish masters (amos). Analyzing entries for the nearly 150 people registered reveals ways that intersectional status and identity affected the experience of registration and the strategies for providing personal information to the Spanish notary. The declarations and omissions contained in the document highlight personal choices that people made to preserve their independence and that of their families. The social and economic independence displayed by many oficiales contrasts with the silence of individuals who lived and worked in the households of wealthy and powerful Spaniards, navigating unequal and enmeshed relationships. The range of individual experiences and statuses evident in the 1582 registry helps explain why the restrictive goal of the proceeding failed in the following years, as well as why a free Afro-Peruvian community did not flourish in Cusco during the later colonial period.