A portion of people with mental illnesses who are arrested are diverted to mental health courts (MHC) where they work with teams of treatment and court staff rather than serving time in custody. This study investigated the association between the relationship with caseworkers and outcomes. MHC participants were recruited to participate in structured interviews on their perceptions of the bond and conflict with their MHC caseworkers. Regression models tested associations between relationships with caseworkers and program retention, service use, and number of days spent in jail. Perceived conflict with caseworkers was higher among participants who were terminated or missing from the MHC. Participants who perceived less conflict with caseworkers utilized more services and spent fewer days in jail. The perceived bond was significantly associated with service use. Caseworkers with clients who are in the criminal justice system should be mindful as conflict arises and implement strategies to effectively manage conflict.