Linkages to services for HIV-infected inmates are critically important; however, little is known about the challenges faced by staff coordinating these linkages. This qualitative evaluation describes the challenges and strategies of frontline staff involved in HIV-related services for inmates and releasees participating in the Centers for Disease Control and Prevention/Health Resources and Services Administration Corrections Demonstration Project. Eight focus groups were held during a national meeting of community-based organizations. Content analysis revealed multiple themes. This evaluation emphasizes the lack of and difficulty obtaining services for this population. Staff recognize the role of security and safety when working in facilities and have identified methods to coordinate and communicate to facilitate their work. Communication with key partners and colleagues is important to understand the challenges and identify strategies; however, political advocacy is important for increased awareness and resources. Consideration of these issues within an ecological framework may help frontline staff translate findings to practice.