This study examined the perceived relationship between military service and the risk of homelessness after discharge and identified specific aspects of military service that homeless veterans experience as having increased their risk for becoming homeless. A cross-sectional survey was conducted among 631 homeless veterans enrolled in the VA Therapeutic Employment Placement and Support Program from January 2001 through September 2003. Associations of sociodemographic characteristics, clinical status, and military service characteristics (independent variables) were examined in relation to perceptions of increased risk for homelessness and time to first episode of homelessness after leaving the military (two dependent variables), using analysis of variance, logistic regression, and multiple regression statistical analyses. Fewer than one third (31%) of the homeless veterans in this study reported that military service increased their risk for homelessness—either somewhat (18%) or very much (13%). Among those veterans who perceived military service as increasing their risk for becoming homeless, the three aspects of military service most commonly identified included a) substance abuse problems that began in the military (75%), b) inadequate preparation for civilian employment (68%), and c) loss of a structured lifestyle. The relatively small proportion of homeless veterans who attributed homelessness to their military service, coupled with the long 14-year average lag time between discharge and their first episode of homelessness, is consistent with epidemiological data suggesting that military service itself does not substantially increase the risk for becoming homeless among veterans.