Prisoner reentry is a stressful process and many prisoners return to behaviors that led to incarceration upon community reentry. We assess how individual-level vulnerabilities interact with system-level barriers that impact the community reentry process. An additional area explored was the impact of reentry services on risk behavior (i.e., sexual risk and substance use). Fifty-one (22 men, 29 women) primarily minority adults returning from the county jail or state prison participated in 4 focus groups in Febuary 2010. Participants took part in tape-recorded focus groups facilitated by research staff trained in qualitative research methodology. Participants reported that a lack of discharge planning led to poor community reentry (basic needs such as stable housing and employment were not met). As a result of a difficulty in accessing services to meet basic needs, many participants used drugs or engaged in sex for drugs, money, or transportation early in the community reentry process. Given the individual-level vulnerabilities of prisoners, they are more likely to reengage in risk behavior, which increases the risk of acquiring and transmitting HIV, reengaging in substance use, and recidivism. In summary, discharge planning should focus not only on sexual and substance use risk reduction, but also confirm that basic needs are met soon, if not immediately, upon release and subsequent community reentry.