This article explores the factors related to jail recidivism among clients receiving case management services who were seriously mentally ill, homeless, and former inmates in a large urban jail. The authors interviewed six case managers about 51 clients and examined the use of treatment stipulations as a condition of probation, clients' major diagnostic and behavioral problems, and case management strategies. Clients whose case managers actively sought legal stipulations to case management as a condition of probation and parole were more likely to return to jail. Implications for service planning and future research are discussed.