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This study aimed to explore the life circumstances and social service engagement of a group of individuals with frequent jail admissions in New York City. In-depth interviews (n=20) were conducted at Rikers Island Correctional Facility with persons identified as “hotspotters” who had entered the jail system at least 18 times in a six-year period. The interview guide included questions on: criminal justice involvement, housing, physical and mental health, and social service utilization. Interviews were audio recorded, transcribed, and thematically coded for analysis. The majority of participants were black men with a median age of 42 years. Participants reported high levels of mental illness, substance use, and homelessness. Nearly all described extensive contact with social services. Participants described cycling through jail, homeless shelters, and hospitals, and reported the function of each was, in many cases, indistinguishable. Participants described an “institutional circuit” that promoted a state of permanent instability characterized by rotating involvement with custodial institutions. Exiting the institutional circuit requires the ability to navigate complex bureaucratic systems; however, without structural reorganization in social service delivery and an emphasis on permanent housing, participants in this group are unlikely to be able to break the cycle.