Abstract: The current literature does not account for how homeless experiences in combination with military sexual assault (MSA) are associated with posttraumatic stress disorder (PTSD), depression, and physical health among military veterans. The survey sample included 251 female and 1,249 male U.S. Armed Forces veterans in San Francisco, CA, and Chicago, IL, who reported their housing status during the past 3 months. Three subgroups emerged: housed, those experiencing broad homelessness (e.g., home of another person, hotel), and those experiencing literal homelessness (e.g., shelter, abandoned building). Analysis included (a) six multivariable logistic regressions to understand the relationship of homelessness and mental and physical health and (b) six moderation multivariable logistic regressions demonstrating the interaction of MSA, homeless experiences, and mental and physical health. Female veterans who experienced literal or broad homelessness and MSA were more likely to have PTSD, depression, and/or physical health symptoms than those who were housed and had not experienced MSA. Male veterans who experienced literal or broad homelessness and MSA were more likely to have PTSD, depression, and/or physical health symptoms than those who were housed and had not experienced MSA. Findings demonstrate the cumulative effect of homelessness and MSA, highlighting the need to assess for MSA among veterans experiencing homelessness, to provide trauma-informed care within homeless services, and to support veterans in achieving secure housing.