Disseminated cutaneous herpes zoster (DCHZ) is an atypical presentation of herpes zoster (HZ) that mainly affects immunosuppressed patients. Given the potential risk for visceral fatal involvement, prompt recognition of this condition is crucial. In this case report, we present the case of a 90-year-old male with chronic lymphocytic leukemia under chlorambucil treatment who presented to the emergency department with multiple, converging, crusted papules on his face. He was misdiagnosed with a drug eruption and hospitalized after switching the antibiotic therapy. After one week, the lesions spread in a cephalocaudal pattern, affecting both the trunk and limbs, following which the Dermatology team was consulted. We performed an HZV smear test and initiated acyclovir. Unfortunately, the test was positive, and DCHZ was confirmed. The patient died one week later due to pneumonitis which evolved into a severe acute respiratory distress syndrome.