Whilst the majority of people released from prison in England and Wales return to private places of residence, a significant minority are required to live in Approved Premises as part of their post-custodial licence conditions. The purpose of this paper is twofold: first, it provides an insight into life inside Approved Premises. This subject has largely been neglected in research to-date, despite Approved Premises being important sites of supervision for many people leaving prison. Second, it explores the quality and dynamics of supervisory relationships between members of hostel staff and residents. Based on fieldwork in two Approved Premises, the findings indicate that, although formally equivalent, people subject to penal sanctions may experience and view these sanctions in markedly different ways. Seemingly innocuous variation in policies and practices at a local level, such as open or closed staff office door policies in Approved Premises, can in fact play a pivotal role in the facilitation or hindrance of constructive supervisory relationships, in shaping rehabilitative regimes, and ultimately, in supporting people's successful transitions from prisons to the community.