This study addressed which factors expert clinicians consider crucial in successful completion versus dropout in the mandatory forensic psychiatric treatment of psychopathic patients in the Netherlands. Eleven clinicians were interviewed about patient characteristics, treatment (provider) characteristics, and other factors they deemed associated with failure (transfer to another facility) or completion. The interviews were coded using the guidelines of Consensual Qualitative Research (CQR). Overall, extremely high scores on Psychopathy Checklist–Revised (PCL-R) Facets 1 (Deceitful Interpersonal Style) and 2 (Defective Affective Experience) were thought to impede treatment retention, particularly by its negative impact on motivation and therapeutic relationship. Older patients, those with a prosocial network, and/or patients with comorbid borderline traits appeared to fare better. Treatment success was deemed more likely when treatment goals and expectations are stipulated in a concrete fashion, when an extended and gradual resocialization trajectory is offered, and the treatment team is expert, cohesive, and stable.