In 2011, Correctional Services Canada closed Canada’s oldest prison in continuous use, Kingston Penitentiary, as part of a larger reorganization and distribution of Canadian prisons. This thesis considers the abandoned prison site as an opportunity for productive and strategic architectural imagination. Through a series of modifications of the old prison -- removals and insertions of new buildings, and thorough redefinition of the grounds and buildings, in particular to do with the way the prison is inserted into its surrounding neighbourhood -- architecture here serves to support new thinking about correction and reformation.