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Military service has been explored as both a turning point towards desistance, as well as a life-course event that may subsequently lead to negative outcomes. An especially important area of inquiry for criminally involved veterans centers on the developmental trajectories by which some individuals with criminogenic risk self-select into the military, and if military service may also lead to criminogenic risk for others. The purpose of this study is to expand on extant literature by examining the narrative life-course accounts of criminally involved veterans in order to better understand these trajectories. The current study draws from qualitative life-course interviews completed with an availability sample of 90 criminally involved military veterans. Utilizing an approach inspired by grounded theory, the current study explores deviance across the life-course in several ways, including (1) biographical trajectories of deviance, (2) narratives of deviance pre-enlistment, during active duty, and after military service, and (3) contextual underpinnings of how the military may influence trajectories of deviance. Results reveal four distinct trajectories of deviance for this sample, as well as ways in which pre-military deviance, social controls, and military culture and experiences can all play a role in the life-course trajectories of criminally involved veterans.