Penal authorities and society in general perceive prisoners as untrustworthy. Much of the administration of punishment constitutes the assessment and management of the risks that prisoners pose. In this article, I explain how Ukraine balances the noble goals of prisoner reintegration with an inherent mistrust of prisoners. Drawing on a semi-ethnographic study of a medium-security prison for men, I discuss how, in anticipation of their freedom, prisoners also calculate their perceived risks. Through examination of how prisoners assess their vulnerability to risky behaviour and opt out from gradual release, I argue that prisoners as well as the state often deem themselves untrustworthy subjects. Furthermore, I discuss the roles of the informal prisoner society and (paucity of) prison’s rehabilitative efforts in prisoners’ decisions concerning their transfer into semi-open conditions. I argue that, rather than being an alternative – and even a threat – to parole, gradual release, supported by rehabilitative and developmental programmes, constructive services and temporary leave schemes, should become a path to release, including release on parole. Prisoners and staff alike should not make an unfair and unconstructive choice between ‘less risky’ parole, because of its loose surveillance, and more failure prone (for prisoners) and blame risky (for staff) gradual release.