This chapter explores the impact and challenges of adopting a trauma-informed approach in a prison-based democratic therapeutic community Enhanced Assessment and Preparation Unit, and therapy wings, from the perspectives of those who live (written in italics) and work there. Those in custody may well have experienced adversity which impacted on their life pattern. The context in which each person is located can affect their ability to address their past and process any unresolved trauma. By providing structure and most of all safety, the residents in a democratic therapeutic community (DTC) can consider their previous responses and what had led to their present situation. A more naturalistic setting can allow previous problematic behaviour patterns to be demonstrated and alternatives practised. A DTC provides a culture of enquiry, in which decisions can be considered and their consequences tolerated. Therapy within a custodial setting allows for the exploration of the meaning of previous responses, and the impact they had on others in a safe environment. One resident will illustrate this through his journey in a DTC. Further, the chapter will discuss the challenges of a compassion-focused approach within a custodial setting and with residents who, although they volunteer for the intervention, would rather not be incarcerated.