What happens when medieval depictions of gender-crossing saints get refracted through a transgender prism? Focusing on objects and artifacts associated with St. Eugenia of Rome, this article considers the extent to which medieval artists confronted the genderqueer potential of Eugenia's legend. Often the saint was overtly feminized, patently obscuring her road to sanctity as a gender crosser. But sometimes the crossing itself was rendered at least partially visible—notably in scenes representing the moment when, after a period living as a male monk, Eugenia is placed on trial and forced to reveal her “true” identity as a woman. Some depictions of Eugenia may therefore resonate with more recent expressions of queer and trans identity. This prompts critical reflection on the concepts of passing and trans visibility in histories of transgender.