This qualitative study explored the dynamics of adolescent HIV risk through focus group interviews of male and female adolescents at an Alabama juvenile detention facility, key informant interviews, and through interviews of HIV-positive and -negative adults in institutional settings and public health clinics in Alabama. The interviews revealed that commodified or unprotected sex with multiple partners was a common risk activity for male and female adolescents, with a related high risk of sexually transmitted disease. The adolescents were aversive to condom use and lacked knowledge of the dynamics of HIV transmission. Bisexually behaving males who engaged in same-sex prostitution for money or drugs viewed female partners as the source of HIV infection. Illicit drug activity and risky sexual behavior were highly related to economic and status anxiety. Experiences of healthcare were often coercive or were undermined by negative perceptions of health professionals. These negative perceptions and avoidance or lack of access to healthcare compounded the already high risk of sexually transmitted disease for this group of adolescents.