In May 2019 the photographic cellphone application Snapchat released two company-generated image filters that were officially dubbed “My Twin” and “My Other Twin,” though users and media labeled them as feminine and masculine, respectively. While touted in most commentary as a “gender swap” feature, these digital imaginaries represent a unique opportunity to consider what features contribute to classification of faces into binary gender buckets. After all, the commonly considered “male” filter makes various modifications—including a broader jaw and addition of facial hair—to whichever face is selected in the photograph. It does not ask and cannot detect if that face belongs to a man or woman (cis- or transgender) or to a non-binary individual. Instead, the augmented reality that it offers is a preprogrammed algorithmic reinscription of reductive gendered norms. When interacting with a novel face, humans similarly implement algorithms to assign a gender to that face. The Snapchat “My Twin” filters—which are not neutral, but rather human-designed—offer an analyzable projection of one such binarization, which is otherwise rarely articulated or visually recreated. Here I pair an ethnographic exploration of twenty-eight transgender, non-binary, and/or gender diverse individuals’ embodied experiences of facial gender legibility throughout life and with digital distortion, with a quantitative analysis of the “My Twin” filter facial distortions, to better understand the role of technology in reimaginations of who and what we see in the mirror.