Objective: We examined the relationship between frequency of incarceration and preincarceration risk behaviors and determined the demographic factors associated with risk behaviors among a sample of African American inmates.Methods: We surveyed 229 (102 female and 127 male) randomly selected inmates. Risk behaviors between inmates serving their first prison sentence and those who had been incarcerated in prison more than once were compared using the chi2 test. Multivariate logistic regression analysis was used to determine factors associated with risk behaviors.Results: For most risk behaviors, there were no significant differences between inmates serving their first prison sentence and inmates incarcerated more than once; however, male inmates who had been incarcerated more than once were more likely to report having had multiple vaginal sex partners (OR, 2.42; 95% CI, 1.10-5.32; P = .03). No demographic variable was found to be independently associated with risk behaviors.Conclusions: Frequency of incarceration did not affect preincarceration human immunodeficiency virus (HIV) risk behaviors among this sample of African American inmates. HIV prevention efforts should be directed at addressing the individual and structural factors associated with high-risk behaviors among African Americans.