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African American men are at high risk of human immunodeficiency virus acquisition. Condom breakage is an understudied aspect of their sexual protective behavior. This study identified user errors leading to condom breakage using an event-specific analysis among young African American men newly diagnosed with a sexually transmitted disease (STD).Recruitment occurred in a publicly funded STD clinic located in a metropolitan area of the Southern United States. Of 296 African American men screened as eligible, 271 (91.5%) agreed to participate. Men completed a self-administered questionnaire. Men reporting condom use with men were excluded from the analysis, leaving an analytic sample of 264 men. The recall period was for the last time men used condoms for penile-vaginal sex (within the past 3 months).More than one-fifth (21.2%) reported condom breakage. Each year of advancing age decreased the odds of breakage by 10% [adjusted odds ratio (AOR) = 0.90, 95% confidence interval (CI) = 0.81–0.99, P = 0.028]. Men who had used an oil-based lubricant were more than 3 times as likely to report breakage (AOR = 3.21, 95% CI = 1.48–7.00, P = 0.003) and those who completely unrolled the condom before putting it on were also about 3 times more likely to report breakage (AOR = 3.34, 95% CI = 1.76–6.50, P = 0.0001). The breakage rate for men indicating both errors, i.e., use of an oil-based lubricant and unrolling the condom before application, was 54.5% compared with 33.3% among those indicated either error, and 12.8% among those indicating neither error. Attributable risk for the 2 errors combined was 39%.Condom breakage among this sample of men at high risk for human immunodeficiency virus infection was common. This problem could be mitigated by counseling men to avoid the use of oil-based lubricants and by teaching them basic condom application skills.