This paper analyses policy documents and interviews conducted in federal prisons to trace the emergence and early effects of Canada’s recent wave of groundbreaking trans correctional reforms. I show that prison authorities were forced to adopt more inclusive policies due to the legal, financial, and reputational risks generated by new trans rights protections. Yet, by examining what rights both enabled and foreclosed once they materialized in the everyday of prison life, I argue that reform’s implementation was fraught with ambivalence. Namely, this ambivalence was felt by the correctional administrators tasked with translating nebulous policy principles into concrete guidelines; by staff, whose front-line duty involved weighing rights against risks; and by trans prisoners, who grappled with how to balance their new entitlements with risks and uncertainties. What trans correctional reforms reveal, then, is that rights and risks are caught in an ambivalent and co-constitutive relationship in Canada’s regime of prison governance.