Many jurisdictions are focusing on digital transformation and outlining strategies for the smart prison and technology driven penalities. We argue that the data produced and used by digital technologies in this context are reciprocally constituted and that the emphasis on digital transformation shifts how penal subjects are constituted, managed, and remembered. We outline the key components of contemporary correctional digital transformation strategies and show how these changes range from platformization to investments in digital infrastructure to the automation of decision-making processes. We demonstrate how these governance logics produce a series of 'penal paradoxes' that are poised to alter penality.