The article discusses the interaction between the Winnebago County Jail in Rockford, IL, and hospice service providers who cared for a terminally ill inmate. This first-time partnership raised a number of issues faced by corrections facilities with aging populations concerning the appearance of preferential treatment and balancing security issues with meeting the needs of a dying patient. Discussed are the security clearances needed to facilitate this care and an orientation for medical personnel that was provided to familiarize them with the corrections environment. Hospice personnel worked with the administrative and medical staff of the jail to develop and implement a plan of care, as well as to prepare for the increased medical care anticipated during the final stages of the terminal disease. The experience of the hospice and jail staff is recounted in the article as it relates to these various issues.