This study evaluates the prevalence of mental/emotional distress and its specific correlates among people living with HIV/AIDS (PLWHA) in 20 jail systems across the United States. Of the 878 PLWHA jail detainees, 52% had high levels of mental/emotional distress, defined by the composite Addiction Severity Index score. High mental/emotional distress was found to be associated with the inmate living in a city with lower income inequality, lower health ranking, and higher degree of danger. Proximate variables included being female, bisexual orientation, poorer physical health, and increased severity of substance abuse. Inmates in jails with accredited health services and those satisfied with family support had lower mental/emotional distress scores. These findings indicate the need for expanded mental health assessment of PLWHAs entering jail.