High rates of HIV, STD and hepatitis and associated risk behaviors have been documented among persons entering correctional facilities. However, there is a paucity of data on risk behaviors after release from custody. This study documents risk behaviors and informs intervention development targeting young men leaving incarcerated settings. We enrolled and interviewed 106 men from five prisons up to 60 days prior to their release from prison and interviewed them again four times after their release (at 1-week, 1-, 3- and 6-months). At enrollment, men were 18-29 years of age. Nearly 54% identified as African American, while 27% identified as White, 10% identified as Hispanic/Latino and 10% identified as "other". Approximately 83% had been incarcerated multiple times, 37% reported a prior STD diagnosis and their mean lifetime number of sex partners was 36 (median = 20). Many reported multiple sex partners and inconsistent condom use after release. A significant decrease in condom use during vaginal sex with primary committed female partners and in oral sex with both committed and casual female partners after release from prison were reported from 1-6 months. These young men are at sexual risk of HIV, STD and hepatitis infection after release from prison. Interventions are needed to prevent this population from acquiring and transmitting HIV, STD and hepatitis.