The 21st Century has seen the continuation of armed conflict, exposing military personnel to the rigours of warfare and the challenges of transition back to a civilian identity. There has been a renewed realisation that there exists a sub-group within the criminal justice system (CJS) of veterans and whilst the exact figures are debated, their presence is not. This thesis seeks to capture the perspectives and experiences of veterans who are identified as exoffenders and those having been employed in the CJS as practitioners. The super-structuralist concept of the CJS collectively represent services of a ‘total institution’ that have shared similarities and differences to life within the ‘total institution’ of the Armed Forces. The life stories of the participants indicated that whilst one veteran life story trajectory (veteran practitioner) appeared to be able to adapt during the transition to a civilian identity successfully, there was evidence that the other veteran life story trajectory (veteran exoffender) found themselves segregated and isolated from a familiar veteran identity with few resources to survive the experience unscathed. This exploratory qualitative study provides emancipatory evidence that the process of entering the CJS as offenders often fails to address the origins of their criminal behaviour or from the wider social context that creates a cyclical response. The veteran practitioners appear to hold a crucial insight into the issues and seek to progress the CJS’s need to expand its knowledge base on the identification, diversion and management of veteran offenders. The study was theoretically informed through the use of reflexivity to articulate the internal and external dialogue of what is known and how it is known in understanding the lived experiences of 17 participants. Life stories were collected from in-depth interviews across the United Kingdom. The life stories were analysed thematically, providing insight and understanding through the elicitation of narratives derived from the contours of meaning from the participants’ (veterans) experiences and enunciating the two separate life story trajectories into the CJS. The findings of this study indicate the participants need to belong and explores how their veteran identity instilled in them both a source of strength and a feeling of anguish, as their new lives could not offer the same security and sense of belonging. The negative consequences of being identified as an offender often resulted in the emergence of stigma and associated shame upon themselves and their families. The life stories demonstrated disparities between the attempted empowering philosophies of the veteran practitioners and the practices imposed generally by the CJS. There were numerous examples of how the veterans’ prior exposure to the institution of the Armed Forces had shaped their experiences and engagement with the institutions of the CJS. Both sub-groups of veterans constructed positive ownership of their veteran identity which at times served to counterbalance their negative experiences of transition from military to a civilian identity. These constructions of their experiences highlight the vulnerability of this sub-group within the CJS and the failure of the system and wider society to address the consequences of military service on some veterans. This research raises the issue of the ‘fallout’ from the recruitment of youth from communities where established socio-economic deprivation has created fertile recruitment grounds for the Armed Forces. The analysis identifies a pragmatic need to address the gaps within the research literature as well as multi-agency working, in order to expand veteran peer support schemes. The voice of the veteran has been overlooked within the positivist research approach, this study seeks to capture the viewpoint of the veterans through reflexive exploratory research undertaken by a veteran researcher to understand the phenomena. Researching the experiences of veterans’ experiences of the CJS presented ethical and methodological challenges. The study has provided new knowledge and understanding that can be disseminated and used to improve current practices and policies.