Most of us, understandably, are fearful of crossing the boundary from lucidity to psychosis or from legality to criminality. Some of us manage to cross both and these individuals we call mentally disordered offenders (MDOs). As a society we invest significantly in forensic mental health services to assess and treat these people but what do we get in return? The outcomes are good in terms of public safety but poor when we examine social connectedness and premature mortality. In forensic psychiatry we work across the boundary of health and criminal justice systems. While more is required to improve the outcomes of MDOs, the real challenge lies in reconsidering some of our working practices and linking health and criminal justice practitioners to improve offender care and outcomes. Recommendations to improve prisoner mental healthcare in Scotland have been made but not fully enacted; and successful working models which focus on consultation and joint working between health and criminal justice such as the Serious Offender Liaison Service or Problem Behaviour Clinics have been developed but rarely applied. Lastly, there is the quest for the Holy Grail – a medication to reduce offending. This is currently being explored with regards to a specific diagnosis in a randomised controlled trial for Attention Deficit Hyperactivity Disorder in young offenders.