Objective Older adults are increasingly involved in the criminal justice system, yet there is limited research regarding their needs and experiences. This study examined differences in psychosocial experiences and reincarceration between older and younger adults with psychiatric disorders involved in the criminal justice system. Methods Participants (N = 80) were recruited from two mental health courts in the midwestern United States. Bivariate analyses examined age-related differences in psychosocial experiences and reincarceration between younger and older participants. Results Older adults, on average, experienced more treatment adherence and fewer probation violations than younger adults during the 6-month follow-up; however, they experienced comparable risk for reincarceration. Older adults' substance use, service use, housing instability, and program retention were similar to their younger counterparts. Conclusion Despite older mental health court participants' treatment adherence and reduced probation violations, they are at risk for incarceration, substance use, and housing instability.