While every slave state except Louisiana limited free Black testimony in cases involving whites, and most barred it completely, several jurisdictions with slavery, including three in the Upper South—Delaware, Maryland, and D.C.—allowed at least some free Black testimony in cases involving whites at least some of the time. Historians and legal scholars have largely overlooked the phenomenon of free Black testimony in the South, outside of Louisiana. In this article, I argue that courts in the Upper South allowed some free Black testimony in cases involving whites in part because allowing (limited) Black testimony enabled courts to access the truth (slightly) more freely, thereby increasing the law's legitimacy. The exceptions to the general bar against Black testimony in cases involving whites also demonstrate the diversity of legal trends in the antebellum Upper South. In Maryland, the space for free Black testimony shrank. In D.C. and Delaware, it grew. But Southerners long contested the relationship between race and law. Competing pressures to administer a well-functioning legal system and to maintain racial hierarchy exerted force on the white elite. Southern elites, even before the great convulsion of the Civil War, sometimes divided on how best to administer a white supremacist legal regime.