In this article, we explore two related questions. First, under what conditions, if any, can a Black person trust a white person to be a reliable ally in the context of a society founded on racial slavery? Second, under what conditions, if any, can a Black person trust a white person to be a reliable ally in the context of a white supremacist society? We follow Karen Jones and Nancy Nyquist Potter in arguing that allies must not only be competent, (...) conscientious, and accurately self-assess their epistemic capacities, but they must also signal their trustworthiness in advance to those who would trust them. Furthermore, we argue based on our readings of the slave narratives of Mary Prince, Harriet Jacobs, and Frederick Douglass that allies must display social awareness of the social context that they share with those who would trust them and the power dynamics involved in that social context. (shrink)