Each year about 100,000 people return to New York City communities from municipal jails. Although about four-fifths report drug or alcohol problems, few have received any formal drug treatment while in jail. Researchers and practitioners have identified a number of policies related to corrections, income, housing, and drug treatment that may be harmful to the successful reintegration of people leaving jail. In order to explore the challenges to successful community reentry, six focus groups and one in-depth interview were conducted with 37 men and women who had been released from jail or prison in the last 12 months. Participants were asked to describe their experiences prior to and immediately following release from jail. Findings suggest that many people leaving jail are not prepared for release and, upon release, face a myriad of obstacles to becoming healthy, productive members of their communities. We discuss the implications of these findings for programs and policies that promote community reintegration of individuals returning from correctional facilities.