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The relationship between military service and deviance has been well examined across numerous decades and various cohorts of veterans. As it stands, however, scholars and policy makers still lack a complete understanding of the day-to-day events and experiences that inspire deviance and other maladaptive outcomes among this population. This study aims to build upon existing scholarship by exploring the lives of a sample of veterans on probation. As part of a larger grant, pilot data were collected with an availability sample of military veterans living in the state of Illinois. Face-to-face interviews with these military veterans on probation explored how deviant behavior, substance use, relationship quality, violence, mental health/illness, military experience, and criminal involvement impacted their lives before and after military service. Results reveal how life-course transitions, including military service, impact this group’s behavior, potentially adding to our theoretical understanding of why some veterans enter the criminal justice system.