Varicella zoster virus (VZV) reactivation, also known as herpes zoster is common in older adults and immunocompromised individuals and often causes a painful, vesicular rash limited to a dermatomal distribution. On occasion, it can lead to various neurological complications as well. Here we present the case of a young, immunocompetent male in his 20's with a history of primary varicella infection who presented with complaints of a painful rash in the S3-S4 dermatomal distribution. Despite being initiated on the standard oral antiviral dose for two days, he developed a headache and neck stiffness. He was diagnosed with VZV meningitis through the lumbar puncture and cerebrospinal fluid polymerase chain reaction (PCR) assay analysis. The patient reported significant improvement in symptoms following intravenous acyclovir and was discharged with additional oral valacyclovir at a higher-than-standard dosage. Our case highlights that even in relatively low-risk patients, physicians must maintain a high level of clinical suspicion for the complications of VZV reactivation even after beginning the oral antiviral medication.