Background A small portion of Americans account for a disproportionate amount of the incidences of sexually transmitted infection observed over a short period of time. Studies with adults have begun to characterize this population, yet there is very little data on adolescent sexually transmitted infection repeaters (STIR). This study explores characteristics associated with STIR among 102 girls and 93 boys (aged 14–18) court-referred for residential treatment. Methods Background characteristics, substance use disorders, risky and interpersonal behaviors, and history of sexually transmitted infections were collected at intake using valid and reliable instruments. A negative binomial logistic regression was performed to determine the background, risky behaviors, and social patterns associated with adolescent STIR. Results Approximately two out of three adolescents (62%) did not use contraception the last time they had sex, and 15% had at least one sexually transmitted infection recorded in their medical chart. Sexually transmitted infection repeaters entered treatment with higher rates of cocaine abuse (13%) than youth without multiple infections (3%, p < 0.05). History of sexual abuse, having sex with a person who said no, higher exhibitionism, and social estrangement increased the odds of adolescent STIR. Main effects of exhibitionism and social estrangement on increased odds of STIR were more pronounced for sexually abused adolescents. Conclusions The findings suggest a need for incorporating HIV education during residential treatment to improve health outcomes and intervention strategies that further connectedness for youth and victims of sexual abuse.