The elevated rates of HIV/AIDS among inmates are due in part to the high concentration of incarcerated persons with behavioral risk factors for HIV infection. Corrections, public health, and community-based organizations should partner to take full advantage of the opportunity to maximize effectiveness and efficiency in addressing HIV/AIDS in inmate populations. The purpose of this study is to document issues inhibiting collaboration, service delivery, and multisite evaluation as identified by members of the U.S. Centers for Disease Control and Prevention/Health Resources and Services Administration Corrections Demonstration Project (CDP). Examining the barriers (and identifying ways to resolve them) is important in developing and maintaining successful programs that ultimately benefit HIV-infected inmates and the communities to which they return.