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Herpes zoster (HZ) results from reactivation of a latent varicella zoster virus (VZV) infection. Clinical manifestations are more common and possibly severe in immunodepressed patients, such as cancer patients. Indeed, HZ can even lead to life-threatening complications. We report the case of an atypical presentation of HZ in an advanced urothelial cancer patient, presenting with long prodromal symptoms and late vesicular eruption. Given the atypical presentation of HZ reactivation among some immunocompromised patients, this case emphasizes the need of clinical suspicion for HZ as differential diagnosis. Furthermore, clinician awareness of prevention of HZ with the recombinant zoster vaccine (RZV) in immunodepressed individuals is also critical to minimize the risk of disease activation and associated morbidity in such patients.