Varicella Zoster (shingles) virus is a double stranded DNA in the Herpesviridae family that can present as both chicken pox and as shingles. The virus enters through the respiratory system, replicating in the nasopharynx, and causes a viremia upon primary infection. Varicella Zoster spreads to other organs and often lies dormant in the dorsal root ganglion. Reactivation of the virus is more common in older or immunocompromised patients and often presents as a painful vesicular rash in a unilateral dermatomal distribution with possible concurrent radiculopathy. A rare complication of herpes zoster is urinary dysfunction. We report a case of a 42-year-old patient diagnosed with herpes zoster whose primary complaint was left buttock pain and a maculovesicular rash in the S2-S4 dermatomal distribution. She was prescribed Valacyclovir and began to experience urinary retention two days after starting the medication.