This paper develops an understanding of gender as something fundamentally technological, and as such broken. Drawing on the technological undercurrent in current posthumanist feminist theory, it puts into play a vocabulary of malfunctioning, broken, vulnerable technologies, and in particular uses the term ‘glitch’ to account for machinic failures in gender within the digital domain. As an intriguing example of the technologies of (trans)gender, the core example consists of the social media presence and public transition of Isabella Bunny Bennett — a musical performer and a member of the U.S.-based band Steam Powered Giraffe. Drawing on how glitch is understood as an accidental error and a critical potential in aesthetic practices, the article is a contribution to what recently has been coined ‘glitch feminism.’