The U.S. judicial and correctional system supervises many individuals experiencing mental illness, homelessness, or both - populations with high rates of recidivism and unmet health needs. This phenomenological case study explores these issues from the perspective of system-involved individuals. By examining how the system addresses - or fails to address - mental illness and housing instability, this research highlights opportunities to reduce recidivism and improve support for reentry through informed, person-centered interventions.