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Dramatically increasing incarceration rates in the United States have led to large concentrations of formerly imprisoned people in poverty-stricken urban areas. Therefore, identifying ways to belp inmates who exhibit multiple, serious problems and who are at great risk of experiencing poor postrelease outcomes is especially important to urban communities, as well as to service providers and policymakers concerned about these communities. Our research provides evidence about the effectiveneess of one strategy, called Health Link, which recruited adult women and adolescent men while they were incarcerated in a New York City jail and offered case management services during the especially challenging first year after release. About 1,400 participants who enrolled during a 3-year period were ramdomly assigned either to a group that was eligible for intensive discharge planning services and community-based case management services or to a group eligible for less-intensive discharge planning and no community-based services. We investigated whether the availability of these services reduced rates of drug use, HIV risk, and rearrest. Using data from interviews and bair analysis to measure impacts during a 1-year follow-up period after clients’ release from jail, we detected increased participation in drug treatment programs and weak evidence for reduced drug use. However, we did not observe reductions in rearrest rates orin activities with high risk of HIV infection. We conclude that a well-executed case management program can make modest differences in a few short-term outcomes of former inmates. However, the intervention did not lead to the hoped-for changes across a range of outcomes that would clearly indicate greater success in community reintegration or improved health.