A 46-year-old man with a history of oral herpes, chronic pain, and a remote history of vasectomy presented with an acute onset of saddle anesthesia and numbness involving the perineum, scrotum, and dorsum of the penis after recent travel to Florida. He was initially evaluated by urology and empirically treated for presumed prostatitis with a course of Bactrim. Urine culture and Prostate-specific antigen (PSA) were unremarkable. He also reported intermittent, holocranial headaches 2/10 in intensity, relieved by over-the-counter medication. He was afebrile and had no rash or leukocytosis. His exam was otherwise normal. CSF analysis demonstrated a lymphocytic-predominant pleocytosis with markedly elevated protein (234 mg/dL), and PCR was positive for varicella-zoster virus (VZV). Brain MRI revealed post-contrast enhancement in the posterior right insular region, suggestive of VZV-associated vasculopathy. And MRI neuraxis showed a 3.5 x 2.5 mm nodular area of post-contrast enhancement within the posterior right paramedian aspect of the spinal canal at the level of the L2 vertebra located along the posterior margin of the thecal sac of uncertain significance, post lumbar puncture. He was treated with intravenous acyclovir for 14 days and oral prednisone for 5 days. One week later, he developed left-eye panuveitis. Repeat MRI of the brain and orbits showed no new or significant abnormalities. Acyclovir therapy was extended for a total duration of 4 weeks and was continued on a steroid taper.