In 1549, Juana Gelofa Pelona, an enslaved African woman, was a witness in a legal case in the city of Santo Domingo, on the island of Hispaniola. The defendant, Francisco Bravo, was accused of killing his wife, Catalina de Tinoco, and presented Juana as his witness to testify on his behalf. Both Francisco and Catalina had been Juana’s enslavers; and, Catalina's family, in whose possession Juana had lived for multiple generations, warned her not to testify in favor of Francisco. Nonetheless, she testified with conviction, despite being threatened and punished severely by her new enslavers who resolved to sell her to another enslaver in a different city to avoid her continuous defiance of Catalina’s family in court. This article proposes that Juana orchestrated her own sale to rid herself of her new owners who wanted to convince her at all cost not to say what she knew. The article also documents aspects of everyday life in sixteenth-century Santo Domingo by highlighting details shared by the witnesses,