Delivered through the medium of a Community of Philosophical Inquiry, this thesis outlines the experience of engaging prisoners in philosophical conversation, thereby articulat-ing the relevance of this type of education for those in long-term confinement. The research, which took place in two prisons, explores the role of prison education, community dialogue and active philosophising in encouraging personal development. With similar populations but contrasting characters, HMPs Grendon and Full Sutton provided the backdrop to grounded, ethnographically-led research. The research design reflects the exploratory nature of the approach. Derek Layder’s adaptive theory has provided a methodological framework, whilst the theoretical framework draws on desistance literature, prison sociology, and philosophical pedagogy to enhance and develop understanding of the emergent themes. However, as a criminological piece of research, it sits within the criminological, and more specifically, prison sociological paradigm. The thesis culminates in a discussion of personal development that articulates the role of education in developing growth identities among prisoner-participants. The research de-scribes the role of philosophical dialogue in developing trust and relationships between and among the participants; the relevance of this type of education to prisoners’ psychological wellbeing; and the significance of the subject-matter to participants’ perspectives. The thesis argues that prison promotes the formation of a hyper-masculine ‘survival’ identity. It goes on to argue that education, and more specifically philosophy education, can play a role in culti-vating growth identities that encourage personal exploration, self-reflection, and development of new interests and skills among prisoners.