We studied a sample of homeless and marginally housed adults to examine whether a history of imprisonment was associated with differences in health status, drug use, and sexual behaviors among the homeless. We interviewed 1426 community-based homeless and marginally housed adults. We used multivariate models to analyze factors associated with a history of imprisonment. Almost one fourth of participants (23.1%) had a history of imprisonment. Models that examined lifetime substance use showed cocaine use (odds ratio [OR]=1.67; 95% confidence interval [CI]=1.04, 2.70), heroin use (OR=1.51; 95% CI=1.07, 2.12), mental illness (OR=1.41; 95% CI=1.01, 1.96), HIV infection (OR=1.69; 95% CI=1.07, 2.64), and having had more than 100 sexual partners were associated with a history of imprisonment. Models that examined recent substance use showed past-year heroin use (OR = 1.65; 95% CI = 1.14, 2.38) and methamphetamine use (OR=1.49; 95% CI=1.00, 2.21) were associated with lifetime imprisonment. Currently selling drugs also was associated with lifetime imprisonment. Despite high levels of health risks among all homeless and marginally housed people, the levels among homeless former prisoners were even higher. Efforts to eradicate homelessness also must include the unmet needs of inmates who are released from prison.