This article sketches key concerns surrounding the digital reproduction of enslaved and colonized subjects held in cultural heritage collections. It centralizes one photograph of a crying Afro-Caribbean child from St. Croix, housed in the Royal Danish Library, to demonstrate the unresolved ethical matters present in retrospective attempts to visualize colonialism. Working with affect and haunting as research material, the inquiry questions how museums and other cultural heritage institutions are caretaking historical violations, identifying themselves as hosting agents, and navigating issues of trust and accountability as they make their colonial collections available online. Speculating about what an ethics of care in representation could look like, the article draws on reparatory artistic engagements with such imagery and proposes how metadata could be rethought as a cataloging space with the potential to alter historical imbalances of power.