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To identify (1) the prevalence of condom breakage, and demographic and sexuality-related differences among young men who have sex with women reporting and not reporting this event; (2) condom-specific behaviours associated with breakage.Young men (n = 278) attending a clinic for treatment of sexually transmitted infections (STIs) responded to an anonymous questionnaire aided by a CD recording of the questions. The samples were screened to include only men who had used a condom during penile–vaginal sex at least three times in the past 3 months. Condom-specific behaviours (including breakage) were assessed using these last three acts of condom use as the recall period. Correlates achieving bivariate significance were subjected to multivariate analysis.Nearly one third (31.3%) of the men reported recent breakage. The breakage rate was 15%. Three correlates significantly distinguished between men who did and did not report breakage. Men who had past STIs were more likely to report breakage (adjusted odds ratio (AOR) 2.08), as were men who also reported condom slippage (AOR 2.72). Less self-efficacy for correct condom use was also significantly associated with breakage (AOR 1.07). Further, three condom-specific behaviours were significantly associated with breakage: allowing condoms to contact sharp objects (AOR 2.6), experiencing problems with the “fit or feel” of condoms (AOR 2.3) and not squeezing air from the receptacle tip (AOR 2.0).Breakage may be common and may occur in a larger context of difficulties with condoms. STI clinics could potentially benefit some men by providing instructions on the correct use of condoms.