This chapter focuses on prisoners are prepared and plan for release often long before they leave prison, and the process of re-entry often involves periods of community supervision, sometimes including semi-secure accommodation. It consider the inter-relationship of prison life and activities and the impact of this on prisoners' outside life. The chapter by Lockwood and Raikes explore tensions experienced by prisoners who are forced to try and reconcile their inside and outside lives by describing the difficult decisions faced by mothers and fathers in prison and the narratives they tell their children about their absence. It explores the process of release by Reeves and Cowe respectively, considering the environment and social interactions between staff and ex-prisoners who are required to live in semi-secure accommodation as part of their re-entry into the community. The chapter continues the exploration of staff experiences, this time in their work supervising parolees and their practice in supporting ex-prisoners to work towards desistance.