In eighteenth-century Saint-Domingue, colonists of all colors had long acknowledged freedom and slavery as flexible categories constructed both socially and legally. By the 1770s, however, laws regulating the boundary between slavery and freedom were undergoing a shift, and freedom was increasingly approached as a strictly legal category initiated only by slave owners and strictly controlled by royal officials. An exactingly defined body of documentary proof became the standard of evidence for demonstrating freedom, and free people of color increasingly needed a “freedom paper trail” to safeguard their status, though what constituted documentary evidence was far from clear. The case of Marie-Victoire Morisseau, a woman of color who claimed freedom, demonstrates the complicated nature of this shift from freedom as a social category to a strictly legal one. It also suggests the mercurial nature of what constituted “proof”, and that sometimes following the letter of the law and producing the required documents was not enough to safeguard liberty.