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Complete oculomotor nerve palsy with pupillary involvement is a neuro-ophthalmologic emergency because it is commonly caused by a compressive aneurysm at the junction of the posterior communicating artery and the internal carotid artery. If left untreated, this condition can be potentially fatal within days. The present report describes a 45-year-old African American woman with human immunodeficiency virus who presented with complaint of new-onset nonspecific headache, acute onset of complete oculomotor nerve palsy, and a dilated pupil of the right eye. Results of standard work-up for aneurysm and other etiologic factors were negative. Ten days after presentation, papulovesicular eruptions occurred over the V1 and V2 dermatomes, revealing herpes zoster ophthalmicus. The present case may be the first to identify a patient with complete ophthalmoplegia with pupil involvement as a pre-eruptive manifestation of herpes zoster. The literature on epidemiology, pathogenesis, clinical presentation, diagnosis, and current treatment options for this rare form of shingles are reviewed.