Adverse cutaneous reactions to medications are not uncommon and may resemble viral infection and vice versa, complicating diagnosis. We describe the case of a 79-year-old male with cholangiocarcinoma with liver and presumed lung metastasis who presented with abdominal pain and was admitted with ileitis with partial small bowel obstruction. He had a widespread papulovesicular rash with hemorrhagic center, mostly on his face, chest, and back. The rash was initially thought to be a drug eruption, but was eventually diagnosed via dermatopathological examination as disseminated varicella zoster virus (VZV) infection. Steroid treatment was discontinued, and airborne precautions were initiated. Polymerase chain reaction for VZV was obtained and intravenous acyclovir treatment was begun. This case of VZV, initially suspected to be an adverse drug reaction, highlights the importance of early identification of a highly infectious lesion and the importance of early infection control measures, given the implications of exposure to VZV for health care personnel.