Liberated and free-born people understood that generating paperwork to record commercial transactions could protect and assure their freedom in the Spanish empire. The chapter explores this know-how through the life of Ana Gómez, a free Black woman who accumulated significant capital over the course of her lifetime and who documented her economic ties as a means of practicing and protecting her freedom. Gómez carefully documented her various economic ties across the Atlantic through paperwork, and astutely measured her trust and social capital with associates when determining whether to record a commercial transaction in writing, or whether to rely on verbal agreements, which she usually only allowed for her credit lines to Black neighbors. The chapter studies how Black women in the late sixteenth-century Caribbean practiced freedom through their economic decisions and protected their freedom through their engagement in legal cultures of paperwork to document their extensive economic, commercial, and social ties.