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In 1924, a racially ambiguous woman named Sarah Simmons escaped from an Alabama prison and later eluded police who searched for her in Chicago at the behest of their southern counterparts. Simmons’ confrontations with and evasion from the state bring attention to the evolving relationship between prisons and slavery and specifically to the ways that the southern carceral regime imported a specific technology from slavery: the runaway slave advertisement. This paper analyzes Simmons' attempts to vanish as part of a longer genealogy of Black women whose freedom was contingent on their ability to thwart the supposedly knowable categories of Blackness.