This article describes a retrospective cohort study of HIV-infected jail detainees cared for at the Cook County Jail Clinic (CCJC), Illinois, between January and June 2007. Continuity care engagement (CCE) was defined as being seen at least once within 6 months after release at the designated continuity clinics. Being highly active antiretroviral therapy (HAART) naïve during or prior to detention, no prior HIV care, and detectable viral load at initial CCJC visit were associated with continuity care nonengagement (CCNE), while being HAART naïve during detention was the only independent predictor for CCNE. Identification of at-risk detainees and interventions based on these findings should be considered to improve CCE in this population.