Introduction:The varicella-zoster virus (VZV) causes Chickenpox and herpes zoster (HZ), commonly referred to as shingles. VZV reactivation occurs within the dorsal ganglion, typically prompted by a compromised immune system. Herpes zoster ophthalmicus (HZO) represents about 10-20% of all HZ cases and occurs secondary to involvement of the ophthalmic nerve, particularly within the V1 distribution. Symptoms manifest with eye pain, tearing, vision loss, and headaches, however more permanent visual deficits can occur if not promptly treated. These symptoms commonly occur 48-72 hours prior to eruption of typical vesicular rash, known as the pre-eruptive phase. Diagnosis in the pre-eruptive phase may be challenging, resulting in increased morbidity.Case Presentation:We present the case of a healthy marathon runner with no medical history who presented with seven days of intractable headache and unilateral eye pain, resulting in profound insomnia and physical debility. The severity of pain caused immense distress and a rapid decrease in functional status for this previously healthy patient. Despite undergoing various pain management interventions and evaluations by both neurology and ophthalmology with unremarkable results, symptoms remained debilitating. The patient eventually developed a small vesicular rash ten days after symptom onset, resulting in diagnosis of HZO. Antiviral therapy led to rapidly improved symptoms. Conclusion:The significance of considering HZO as a differential diagnosis in patients with intractable pain syndromes cannot be overstated, as overlooking this condition may lead to permanent ophthalmologic consequences including vision loss and blindness. Awareness of the prolonged pre-eruptive phase can lead to earlier consideration of HZO, and prompt antiviral therapy.