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A 67-year-old male patient with poorly controlled type-2 diabetes mellitus developed an orbital apex syndrome and anterior cavernous syndrome secondary to herpetic zoster ophthalmicus (HZO), despite being on oral acyclovir. Urgent treatment with intravenous acyclovir led to improvement of the orbital and ocular inflammation but had no effect on the complete ophthalmoplegia and profound visual loss. At the 9-month follow-up visit, the patient had complete unilateral ophthalmoplegia and monocular blindness due to optic atrophy.