The purpose of this randomized controlled study is to evaluate the impact of an intensive 30-hour post-release intervention versus a single jail-based discharge planning session in reducing drug use and drug selling, HIV and STI risk behavior, and rearrest among a population of jailed male adolescents. We are currently completing a randomized trial of a one-year post-release case management intervention for male adolescents. Our experience suggests that a shorter, more intensive intervention may achieve higher retention rates and effectively protect adolescents from returning to drug use, crime or HIV risk behavior in the hours, days, and weeks after they are released from jail. Whether a brief intervention in the two weeks after release from jail is more effective than a single jail-based discharge planning session is an open question. We propose to recruit in the New York City jail over four years 600 male adolescents from Manhattan and the Bronx with a history of substance abuse problems or drug selling, conduct an intake assessment, and then randomize individuals to receive either jail services only or jail and intensive community services. The specific aim of this study is to test the hypothesis that incarcerated male adolescents aged 16 to 18 who receive a jail and community intervention that includes at least 12 hours of jail services and 30 hours of community services in the two weeks after release will be more likely than a randomly assigned comparable group that receives only a discharge planning session in jail to demonstrate at 12 months post-release an increase in involvement in drug treatment, education and employment; and, reductions in the frequency and amount of alcohol and illicit drug use; lower rates of HIV risk behavior; lower rates of involvement in drug sales; and of rearrest. A secondary aim of this study is to compare patterns of drug use and HIV risk behavior among male and female incarcerated adolescents. To achieve this aim we will recruit 240 adolescent females who will complete an intake assessment and receive a jail-based discharge planning session. This sub-study will also be used to tailor the intervention tested in this proposal for adolescent females.