Diagnosis of atypical generalized forms of herpes zoster can be a challenge and may lead to a delay in treatment. Herpes zoster can present with atypical clinical manifestations, some with higher risk of complications that are potentially life-threatening. We describe a patient that presented with several ulcerated papules and plaques in a non-dermatomal distribution in whom disseminated cutaneous herpes zoster was proven by molecular amplification testing. Patients with disseminated herpes zoster should be treated initially with intravenous antiviral therapy, followed by oral acyclovir, valacyclovir, or famciclovir in most adults, with close follow-up. Earlier treatment may reduce the risk of developing complications and progression of visceral involvement. This case adds to the evolving literature related to herpes zoster, especially regarding patients with immunosuppressed status.