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Incarcerated veterans are a subgroup of the justice-involved veteran population that deserves specific focus. In this research, we sought to investigate the life course pathways that led incarcerated veterans into and out of the military and eventually into prison. This allowed an examination of their lives before, during, and after military service to provide deeper understanding of how some of our nation’s heroes have ended up incarcerated. Semi-structured interviews were conducted with 43 incarcerated male veterans in two Midwestern prisons. Preliminary analyses indicate three distinct pathways. The most common pathway was one marked by problems throughout the life course in which incarcerated veterans discussed disruptions in their families of origin, non-compliance in their military service, instability in their relationships and employment, and criminal activity that eventually led them to becoming incarcerated. A second pathway involved prosocial lives until an isolated incident led to their incarceration. The third pathway indicated relative stability until addiction or other problems disrupted their lives and resulted in incarceration. Interestingly, military service itself did not appear related to their criminal behavior and eventual incarceration. Understanding these pathways can help us better assist veterans to prevent and intervene in antisocial and criminal behavior.