A 46-year-old male with a history of sleep apnea and hypertension presented to the emergency department with a 4-day history of a left facial rash. Initially suspected as an allergic reaction, the rash evolved into painful vesicles, prompting further medical attention. Examination revealed a vesicular rash on the left forehead and eyelid, elevated blood pressure, leading to a diagnosis of herpes zoster ophthalmicus (HZO). The patient was noted to have disconjugate gaze, prompting Neurology consultation. Examination by Neurology disclosed decreased abduction of the left eye with no accompanying abnormal cranial nerve findings and no long tract signs, consistent with isolated CN VI palsy. Brain and orbit MRI with and without contrast revealed asymmetric enhancement of the left optic nerve sheath and enlargement and enhancement of the left extraocular muscles. No acute infarcts, hemorrhages, or intracranial abnormalities were identified. Laboratory tests showed triglyceridemia, but was otherwise unremarkable. The patient was diagnosed with infectious optic neuritis and left extraocular muscle inflammation secondary to HZO. Treatment with IV acyclovir for ten days resulted in symptom improvement, including resolution of the rash and diplopia.