Rooted deep in the history of armed conflict and military affairs, the struggles associated with veteran reintegration with their communities is not a new phenomenon. It is a timeless challenge, colored by the era in which the veteran served but with the unfortunate constancy of tensions among veterans and civilians. This chapter briefly reviews veteran-community reintegration experiences during various historical periods before delving into common barriers to veterans’ successful return to civilian life and the role of the community in that process. The chapter then turns to the compound problems facing veterans who have struggled with reintegration while also navigating the fraught process of returning to society after a period of criminal justice involvement. The reintegration process for formerly incarcerated veterans mimics that of formerly incarcerated civilians, but reintegration difficulties for justice-involved veterans may be exacerbated by unresolved tensions related to their military background and community reactions to their military heritage. The discussion concludes with considerations about VTCs ability to aid veterans who find themselves involved with the criminal justice system and how VTCs can promote positive reintegration experiences for veterans and communities.