Varicella-zoster virus and herpes simplex virus types 1 and 2 are neurotropic viruses that can be reactivated after a surgical or stressful intervention. Although such cases are uncommon, consequences can be debilitating, and variable treatment responses merit consideration. We describe a 41-year-old male with a history of varicella-mediated skin eruptions, who presented with continuing right arm pain, burning, and numbness in a C6 dermatomal distribution following a C5-6 anterior cervical discectomy and fusion and epidural steroid injections. The operative course was uncomplicated and he was discharged home on postoperative day 1. Approximately ten days after surgery, the patient presented to the emergency department complaining of severe pain in his right upper extremity and a vesicular rash from his elbow to his second digit. He was started on Acyclovir and discharged home. On outpatient follow-up, his rash had resolved though his pain continued. The patient was started on a neuromodulating agent for chronic pain. This case adds to the limited literature regarding this rare complication, brings attention to the symptoms for proper diagnosis and treatment, and emphasizes the importance of prompt antiviral therapy. We suggest adding a neuromodulating agent to prevent long-term sequelae and resolve acute symptoms.