Abstract: The military-to-civilian transition (MCT) can pose challenges for veterans of the Canadian Armed Forces (CAF), particularly those who have been involuntarily released due to operational stress injuries (OSI), as they often face exacerbated mental health issues and feelings of alienation. There is a pressing need for further research to better understand their experiences and identify effective support strategies. This interpretative study explores MCT experiences of male CAF veterans living with OSIs. Methods: Using purposive convenience sampling, four male veteran recruiters were chosen to use snowball sampling to recruit four male participants. Qualitative data were collected using virtual, semi-structured interviews. Interpretative phenomenological analysis was selected to analyze the data. Results: Six superordinate themes were identified: lack of decompression between stages of transition, interacting with civilians as an unrelatable experience, peer support networks are helpful, realization of changing identity, Veterans Affairs Canada (VAC) requires an acclimation process, and Depart with Dignity (DwD) as having significance in morale. This article highlights various challenges CAF veterans face upon reintegration and merges them with findings similar to previous literature. Additionally, the study presents recommendations based on the analysis and suggestions from the veterans, emphasizing the most significant factors that need further consideration.