Homelessness and incarceration are closely linked among women, and rates of these marginalizing circumstances are increasing. Nonetheless, few studies have examined differences between female inmates who were previously homeless and female inmates who were not homeless prior to incarceration. Results indicated that women who were homeless prior to incarceration were more likely (relative to their non-homeless counterparts) to have experienced childhood molestation, adult sexual assault, and arrests for prostitution and to have been in treatment for substance misuse. Homeless and non-homeless women did not differ significantly on measures of psychological adjustment. Implications, limitations, and suggestions for future research will be discussed.