Individuals with serious mental disorder diagnoses (SMD) are overrepresented in U.S. jails and prisons, returning to custody more often and more quickly than those without these diagnoses. This paper examines the strengths and limitations of existing theoretical interpretations of justice involvement among those with SMD. Further, the paper presents results from in-depth interviews (n = 23) in an effort to direct an alternative theoretical path. Findings indicate people with SMD are not simply subject to the whims of their psychopathology. Instead, they are risk-exposed agents whose arrests are related to early institutionalization, interpersonal conflict, and life circumstances punctuated by socioeconomic marginality. Such findings suggest longitudinal and multi-level theoretical orientations are most appropriate for understanding carceral involvement among individuals with SMD.