A striking feature of the skull base is the pterygoid hamulus known for its bizarre morphology and biomechanical location. Pterygoid hamular bursitis is an inflammation of bursae located between the tendon, muscle, and bony prominences. The minimal objective finding in an apparently normal orofacial apparatus and dependence on the subjective symptoms experienced by the patient with widespread referral pattern often perplexes the clinician. Bursitis should be considered in the differential diagnosis of craniofacial neuralgia, temporomandibular joint dysfunction, and chronic craniofacial pain. Clinical signs and symptoms of this intriguing entity are diverse and multifaceted that can sometimes demand services of clinicians across various specialties considering the anatomic density of the region. Care must be taken to avoid delay, misdiagnosis, and overtreatment.