This dissertation examines how trans vocalists in popular music use performative and digital vocal techniques to reconfigure ideas of authenticity that circumscribe trans subjectivities. Calls for trans individuals to “find their voices” encourage agential vocal self-expression while framing the voice as a sign of trans selfhood and gendered interiority. However, while ostensibly affirming all trans voices in their individual differences, this discourse is organized around ideas of vocal intelligibility that end up reinscribing normative values regarding gender, race, class, and respectability. Trans vocal practices in popular music offer insight into how discourses of trans vocal authenticity discipline and enable sonic expressivity and meaning, and how trans individuals use music, bodily techniques, and digital technologies to navigate these norms. This project studies trans artists whose vocal performances reconfigure ideas of authenticity, arguing that they perform an “ambivalent authenticity” that makes audible the contradictions and multiplicities surrounding trans voices and subjectivities. Trans vocal ambivalence demonstrates how both voice and transness are paradoxically framed as categories of reification and rupture. I work with an unruly archive of artists who use voice and sound to work within and against ideas of legibility and audibility: SOPHIE’s digitally processed hyperpop voices, rapper Mykki Blanco’s vocal shapeshifting, the queer hip-hop vocal parodies of Athens Boys Choir, and trans masculine self-duets by YouTube artists Romeo Ryu Reyes, Charlie Peck, and Jaimie Wilson. Through analyses of musical performance, audiovisual strategies, and popular reception, I demonstrate how trans vocality is a site of ontological, epistemological, and temporal contradiction.