“Transitioning the Theatre Industry” examines the state of trans theatre in Canada. Vibrant creativity abounds in trans, transgender, transsexual, two spirit, and genderqueer communities. Trans artists, particularly those at the intersections of marginalized identities such as trans women of colour, have immense underused contributions to make to Canadian theatre. Yet there is a lack of trans content in theatres, and very few trans artists are able to access careers in theatre. While mainstream trans visibility has increased somewhat, the majority of cultural content about trans people continues to be created by non-trans artists. The voyeuristic biases of non-trans people shape the telling of particular trans narratives with problematic stereotypes. In contrast, at a community level, trans artists are creating compelling work exploring the wholeness of our experiences—not just our surgeries and physical transitions. Theatre presenters are frequently more conservative than their audiences—wide audiences are able to enjoy trans-themed work, although it is also valid for trans artists to make work specifically for trans communities. This article urges support for the development and presentation of trans artists as a priority, yet also explores whether and how non-trans artists can create respectful, nuanced trans characters.