Herpes zoster, known as shingles, typically presents with a well‑defined dermatomal rash, but atypical manifestations can post diagnostic challenges. We present the case of a 55‑year‑old African American woman with a history of childhood varicella‑zoster virus (VZV) vaccination who presented with a painful perianal rash initially mistaken for an allergic reaction. Despite previous vaccination, she developed a series of asymmetric ulcerative lesions with associated itching and burning, extending into the perianal region. Visual inspection revealed vesicular lesions on the right medial buttock, suggestive of shingles.