Background: Adolescents are at high risk of sexually transmitted disease (STD)/HIV infection, and one vulnerable sub-group is African American females. The association between adolescents' previous experience of STD and recent sexual risk behaviors has been ill-defined. Goal: The goal was to examine the associations between adolescents' self-reported history of STD diagnosis and current sexual risk behaviors, prevention knowledge and attitudes, and STD infection status. Study Design: This was a cross-sectional survey. Recruitment sites were in low-income neighborhoods of Birmingham, Alabama, characterized by high rates of unemployment, substance abuse, violence, and STDs. Participants were sexually active adolescent females (N = 522) 14 to 18 years of age. Information on STD history and current sexual behaviors (within the 30 days before assessment) was collected in face-to-face interviews. Less sensitive topics, such as STD prevention knowledge, attitudes about condom use, and perceived barriers to condom use, were addressed via self-administered survey. DNA amplification of vaginal swab specimens provided by the adolescents was performed to determine current STD status. Outcomes associated with past STD diagnosis were determined by means of logistic regression to calculate adjusted odds ratios (AORs) in the presence of observed covariates. Results: Twenty-six percent of adolescents reported ever having an STD diagnosed. Although past STD diagnosis was associated with increased STD prevention knowledge, it was not associated with increased motivation to use condoms. Compared with adolescents who had never had an STD, adolescents with a history of diagnosed STD were more likely to report not using a condom at most recent intercourse (AOR = 2.54; 95% CI = 1.64-3.93; P = 0.0001), recent unprotected vaginal intercourse (AOR = 1.79; 95% CI = 1.15-2.79; P = 0.010), inconsistent condom use (AOR = 2.27; 95% CI = 1.46-3.51; P < .0001), sexual intercourse while drinking alcohol (AOR = 2.09; 95% CI = 1.33-3.28; P = 0.001), and unprotected intercourse with multiple partners (AOR = 3.29; 95% CI = 1.09-9.89; P = 0.034). Past STD diagnosis was associated with increased risk for current biologically confirmed gonorrhea and trichomoniasis (AOR = 2.48; 95% CI = 1.09-5.23; P = 0.030; and AOR = 2.05; 95% CI = 1.18-3.59; P = 0.011, respectively). Past STD diagnosis was not significantly associated with increased risk of current biologically confirmed chlamydia (AOR = 0.78; 95% CI = 0.45-1.37; P = 0.38). Conclusion: Among this sample of female adolescents, past STD diagnosis was an indicator of current high-risk sexual activity and increased risk for two common STDs: gonorrhea and trichomoniasis. Although adolescents may gain factual knowledge from the experience of having an STD diagnosed, they are not applying that knowledge to their current sexual behaviors. Thus, these adolescents remain at risk for subsequent STD infection. Therefore, the findings suggest that there is a need to intensify clinic-based prevention efforts directed toward adolescents with a history of STDs, as a strategy for reducing STD-associated risk behaviors and, consequently, the likelihood of new STD infections.