Annually 700,000 individuals are released from U.S. prison, many at risk for food insecurity and HIV. The association between food insecurity and HIV risk behaviors has been established but not in this population. To investigate this association, we recruited 110 recently released prisoners to participate in a survey. Ninety-one percent of our sample was food insecure; 37% did not eat for an entire day in the past month. Those who did not eat for an entire day were more likely to report using alcohol, heroin, or cocaine before sex or exchanging sex for money compared to those who had at least a meal each day. From this pilot study, released prisoners appear to be at risk for food insecurity, and not eating for an entire day is associated with certain HIV risk behaviors. HIV prevention efforts should include longitudinal studies on the relationship between food insecurity and HIV risk behaviors among recently released prisoners.