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Personality disorder occupies a complex and ethically charged position at the intersection of psychiatry, psychotherapy, law, and public morality. While psychotic illness is widely recognised as mitigating culpability in criminal sentencing, personality pathology is inconsistently treated and frequently regarded in practice as a set of wilful character flaws rather than an unwanted, distressing disorder. This article explores the cultural narratives that shape judicial approaches to personality disorder, examines the evolution of Australian appellate case law, and considers the implications for forensic clinicians and sentencing practice. Drawing on psycho-dynamic and developmental understandings of personality disorder, this article argues for the application of dimensional severity models (ICD-11; DSM-5 AMPD), careful articulation of realistic connections between pathology and offending behaviour, and the reaffirmation of rehabilitation as a legitimate sentencing objective. This article concludes that forensic psychotherapy plays an essential role in challenging cultural fatalism and supporting psychologically informed justice.