Background: A small proportion of people who have serious mental illness and rapid and frequent incarcerations account for a disproportionate amount of overall service use and cost. It is important to describe such individuals, so that services can respond more effectively. Methods: We investigated a cohort of 4,704 incarcerated men and women who were discharged from a correctional mental health service and followed for a median of 535 days. We investigated social, clinical, demographic, and offense characteristics as predictors of return to the service using Cox survival analyses. Secondly, we characterized individuals as high-frequency service users as those who had 3 or more incarcerations during a 1-year period and investigated their characteristics. Results: We found that a higher rate of return to custody was associated with schizophrenia spectrum/bipolar affective disorder (BPAD), personality disorder traits, crack cocaine and methamphetamine use, and unstable housing. Charges of theft/robbery and breach of probation were also positively associated, and sex assault was negatively associated with return to custody. Within a 1-year time period, we found 7.2% of individuals were high-frequency service users, which accounted for 19.5% of all reincarcerations. Conclusion: Identification of the characteristics of those with mental illness in custody, especially those who have high-frequency returns to custody, may provide opportunity to target resources more effectively. The primary targets of intervention would be to treat those with schizophrenia/BPAD and substance use problems, particularly those using stimulants, and addressing homelessness. This could reduce the problem of repeated criminalization of the mentally ill and reduce the overall incarceration rate.