Background, Chronic oral, facial and head pain is a common clinical problem, and appropriate diagnosis and management are a challenge for health care professionals. Patients often will first seek the care of dentists because of the pain's localization in the oral cavity and surrounding structures. This article emphasizes the importance of establishing accurate diagnoses and conducting appropriate triage of the patient with complex orofacial pain. Case Descriptions. The authors present two case reports illustrating the complex nature of oral, facial and head pain, and the potential and actual pitfalls in management of this condition. These representative cases demonstrate how orofacial pain-which appears to be localized in the peripheral dental and oral structures-can have extremely complex etiologies involving other anatomical structures, the central nervous system and psychological factors. The reports point to the need for the expertise of a number of specialists in such cases. Clinical Implications. If the symptoms and clinical findings do not appear to be consistent with typical oral disease, or if standard treatments do not alleviate the pain, the dental clinician must consider other, more complex orofacial pain diagnoses. The dental professional should not hesitate to make referrals to key specialists or to members of an interdisciplinary team at a pain treatment center who have the expertise to appropriately diagnose and manage chronic oral, facial and head pain.