OBJECTIVES: To identify the prevalence of condom use errors among detained female teens and to test two inter-related hypotheses concerning condom failure. METHODS: A cross-sectional survey of 134 female teens recruited within eight detention facilities. Measures were collected using audio-computer assisted self-interviewing. Assessment for the presence of C. trachomatis and N. gonorrhoeae was also conducted. RESULTS: Five forms of condom use errors/problems were common: not discussing condom use with the partner (34.3%), not having a condom when one was desired (48.5%), starting sex before application (21.6%), removing condoms before sex concludes (26.9%), and breakage (32.8%). Significant, associations were found between condom errors/problems and drug/alcohol use. Errors/problems with condom use were significantly higher among teens diagnosed with an sexually transmitted disease (STD) (P = 0.039 for an index measure; P = 0.022 for a single-item measure). CONCLUSIONS: Findings suggest that detained female teens may have experienced multiple condom use error and problems thereby increasing their vulnerability to STD acquisition.