The Veterans Health Administration (VHA) has been increasing efforts to reach out to assist incarcerated veterans. While previous studies have shown strong associations between incarceration and homelessness, few studies have examined distinctive characteristics of incarcerated homeless and non-homeless veterans. National administrative data on 30,348 incarcerated veterans served by the Health Care for Re-entry Veterans (HCRV) program were analyzed. Incarcerated veterans were classified into four groups based on their history of past homelessness: not homeless, transiently homeless, episodically homeless, and chronically homeless. Multinomial logistic regression was used to compare groups on sociodemographic characteristics, criminal justice status, clinical status, and their interest in using VHA services. Of the sample, 70 % were classified as not homeless, 8 % as transiently homeless, 11 % as episodically homeless, and 11 % as chronically homeless. Thus, 30 % of the sample had a homeless history, which is five times the 6 % rate of past homelessness among adult men in the general population. Compared to non-homeless incarcerated veterans, all three homeless groups reported significantly more mental health problems, more substance abuse, more times arrested in their lifetime, more likely to be incarcerated for a non-violent offense, and were more interested in receiving VHA services after release from prison. Together, these findings suggest re-entry programs, like HCRV, can address relevant mental health-related service needs, especially among formerly homeless veterans and veterans in need of services are receptive to the offer of assistance.