This study investigated the role of incarceration in HIV/STD risk among 197 Black men who have sex with men in Massachusetts, USA. More than half (51%) reported a history of incarceration (28% < 90 days in jail/prison; 23% ≥ 90 days in jail/prison). Multivariable logistic regression models adjusted for age and sexual orientation examined associations between demographic, behavioural, social-psychological and cultural factors and incarceration history. Factors associated with < 90 days of incarceration were: unprotected sex with a man, STD history, injection drug use and substance abuse treatment. Factors associated with ≥ 90 days of incarceration were: unprotected sex with a woman, crack use during sex, STD history, injection drug use, substance abuse treatment, depressive symptoms, post-traumatic stress symptoms, HIV fatalism and social capital. Black men who have sex with men with incarceration histories may be at increased risk for HIV/STDs compared to those without such histories. HIV prevention efforts that focus on individual risk and cultural-contextual issues among Black men who have sex with men are warranted.