The provision of mental health services in the correctional system is challenging at best for various clinical, administrative, and structural reasons. Among the complicating factors is the assessment and management of character pathology which either confounds the treatment of more "serious" mental illnesses, e.g. Axis I disorders, and/or presents itself as the primary focus for intervention. In this paper we review the prevalence of personality disorders on the prison mental health services caseload in New York State. We compare inpatient and out-patient rates among the various disorders documented in the prison system, as well as look at these rates within the context of the rates of personality disorder in the state mental health system generally. Assessment of personality disorder will be addressed with particular attention to the confounding influence of the prison environment. Finally, treatment options will be discussed, including discussion of new initiatives that attempt to address inmates with serious mental illness and personality traits that lead to disciplinary housing.