Given the prevalence of both digital media and trans* visibility over the last 20 years, this essay draws parallels between these two forms of seeing and being seen. It will focus on three digital Chilean films featuring trans* characters: El pejesapo (Jose Luis Sepulveda, 2007), Empana de pino (Wincy Oyarce, 2008), and Naomi Campbel (Camila Jose Donoso and Nicolas Videla, 2013). The representations of blurred gender binaries in these films are analogous to their evasion-in the context of "trans-fiction"-of the supposed binary between fiction and documentary genres. In light of recent debates about trans* rights in Chile, and the recent Oscar win of Una mujer fantastica (Sebastian Lelio, 2017), which featured a trans* character, this essay argues for the uniqueness of digital cinema as a site for trans* people in Chile to confront issues of access to political, historical, and aesthetic representation.