A high proportion of those in prison suffer from a mental illness. Whilst in prison there are opportunities for rehabilitation through therapy facilitated through the therapeutic relationship. The aim of this thematic analysis was to uncover the lived experience of therapists working inside prison in an Irish context. How the prison environment affects the therapists, the therapeutic alliance, the working relations with other staff, and the unique nuances it presents have been explored with four therapists working in prisons in Dublin. The challenges from working in an enclosed environment are a plenty which provides insights and opportunities. This research reiterates the need for treatment services in prison and outlining some improvements that could be made for the benefit of clients and staff. Reducing the occurrence of inconsistent sessions, ensuring clients are ready for change and engagement in a therapeutic relationship, and having better facilities overall in the prison would provide a better working environment for therapists and thus a better experience for prisoners.