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This essay argues that Dawoud Bey’s photograph series Night Coming Tenderly, Black (2017) inventively engages the mechanics and metaphors that shape the medium of photography and its material and social history. The work is about the Underground Railroad, and Bey’s dark prints are especially appropriate to his subject, bearing witness to the relative obscurity of the Underground Railroad and intervening in the compulsory exposures of slavery. Night Coming Tenderly, Black draws into view the darkness without which photography cannot exist in the analog forms Bey prefers, and refuses one of the central mythos about photography, namely, that it is “light writing.” Situating Bey’s work in the African American social, historical, and photographic contexts that his installation at the Art Institute of Chicago invited, the essay explores the photographic evidence of the Underground Railroad that does exist, and the ways in which fugitives negotiated their relationship to property and self, and property in self, through the photograph. Finally, the essay considers Bey’s work in relation to the “general strike” of enslaved African Americans that W. E. B. Du Bois argues won the US Civil War. In this context, Bey’s dark images of the Underground Railroad might be said to perform a “general strike” against the conditions through which Black subjects have come into photographic visibility.