This article argues that Black writers throughout the nineteenth and twentieth centuries produced a critical knowledge of how legal documentation functions to produce racialized structures of power and Black vulnerability at law. In literature that reckons with slavery’s legal afterlife, particularly antebellum slave narratives, post-Reconstruction novels, and neo-slave narratives, Black authors frequently represent legal documents as pivotal to legal personhood and theorize how these documents produce vulnerability to violence and dispossession. The adversarial relationship with contract law that Black people have experienced throughout US history has uniquely positioned Black writers to produce a critical knowledge of law’s structures of power. These writers reveal the mechanisms by which legal authorities manipulated the legal contracts that as texts stipulated protections for Black subjects yet in practice failed to accomplish those protections when white legal authorities refused to carry them out. Building on critical race theory and law and literature scholarship, this article proposes a heightened awareness for how race interacts with legal procedure, particularly during the material processes involved in a document’s creation and execution. Focusing on law’s materiality, this article uncovers an understudied literary vein in which Black authors represent documents as materially fragile and vulnerable to destruction in order to theorize law as a series of practices enacted by persons inhabiting bodies marked by race.