From late Victorian Model Housing tenements to the public housing projects of high modernity, western states have attempted to use housing as a tool of moral transformation. This paper investigates the case of a Winnipeg landlord who has recently transitioned their private market apartments towards a drug addiction recovery model, and asks how a new form of rehabilitative capitalism has adopted disciplinary techniques from both the welfare and the carceral state. While the landlord has rebranded into an altruistic entity, forming new relationships with community organizations and various arms of the state, they have simultaneously created polices of confinement for their tenants including curfews, a pass system, rules of partitioning, and mandatory volunteer hours. In a long line of state-led projects that have attempted to use Foucauldian techniques of totalizing surveillance and control, the cracks in the landlord’s rehabilitative project will show where disciplinary power continues to fail and to renovate itself. Interviews with tenants and other actors in the landlord’s network help to understand where this project has met resistance, where it has been accepted, and where it has had to change. Further, the case study explores how confinement has been adopted into the accumulation strategies of private capital, and how rehabilitation creates new subjectivities based on intersecting categories of ‘risk’ in order to justify intervention.