Mental health (MH) care for Italian prisoners and offenders with mental illness is a paradoxical issue. Theory and practice remained unchanged throughout the 20th century, despite radical changes to general psychiatric care. Until recently, Italy had one of the most advanced National Health Service (NHS)-run community psychiatry care systems and a totally obsolete system of forensic psychiatry managed by criminal justice institutions. Not until 2008, after substantial pressure by public opinion and International Human Rights bodies, did the government approve a major reform transferring health care in prisons and forensic hospitals to the NHS. Forensic hospitals were to be progressively closed, and specialized small-scale facilities were to be developed for discharged offenders with mental illness, along with diversion schemes to ordinary community care. Despite some important achievements, three major problem areas remain: this reform happened without changes to the Criminal Code; regions differ in organization and resources for ordinary psychiatric services; and legal/criminological expertise among NHS MH professionals is limited.