In this paper we examine risk behavior, exposure to street outreach, and condom use in samples of injecting drug users (IDUs) and high-risk youth. We used systematic sampling methods to produce representative samples of injecting drug users IDUs (five sites) and high-risk youth (three sites). The populations surveyed engaged in high levels of sexual risk behavior: 20% to 46% reported two or more sex partners in the last month. The majority (62% to 97%) knew someone infected with HIV. Condom use rates approached national health promotion goals for nonsteady partners but not for steady or main partners. Having a condom at time of interview was the most consistent predictor of condom use at last intercourse. Many of the respondents have been in contact with street outreach programs and many acknowledged some personal risk for HIV infection. However, most of the injecting drug users and high-risk youth interviewed (and their sex partners) were still at risk through unprotected sex.