Despite recent advances in the scholarship of history and architectural history, the practice of urban slavery is distinctly understudied in North American archaeology in contrast to plantation archaeologies. This is due largely to the fundamental challenge of investigating urban households, where many individuals of differing social and economic status (free and unfree, Black and white) occupy the same limited space and dispose of their refuse in shared locations, thereby contributing to a highly mixed archaeological record that is difficult—if not impossible—to parse. However, when the researcher pivots to imagining individual entanglements within a shared material world, new interpretations emerge in the noise and dissonance of urban life. This article considers the narratives of three enslaved individuals (two men and one woman) who lived and labored at 87 Church Street in Charleston, South Carolina, during the eighteenth century. Although this is an illuminating approach, traversing archival (archaeological) silences and highlighting individual lives and worlds in the archaeological record demands considerable interpretive caution and care.