Among persons living with HIV/AIDS (PLWHA) experiencing homelessness or imminent risk of homelessness, a history of incarceration may serve as a marker for ongoing risk behavior or health disparities. We examined factors associated with a history of incarceration among HIV-positive clients of housing agencies in Baltimore, Chicago, and Los Angeles (N = 581). We used logistic regression to conduct analyses. Of the 581 participants, 68% (n = 438) reported a history of incarceration: 32% (n = 182) had spent more than 1 year incarcerated. After adjustment for covariates, incarceration history was associated with having ever injected drugs, ever engaged in sex exchange, and ever experienced physical abuse. Incarceration history was also associated with having a detectable HIV viral load, better mental health, and being a biological parent. It was not associated with current risk behavior. Service providers may explore possible increased need for medical support among homeless PLWHA with a history of incarceration.