The characteristic presentation of herpesvirus infections is a vesicular rash. The initial lesions appear as erythematous papules that turn into grouped vesicles and pustules eventuating into crusts. In most cases, the features are so characteristic that a diagnosis can be made by history and physical examination without further diagnostic testing. However, patients who are immunosuppressed (including those with hematologic malignancies) often have atypical presentations of herpesvirus infections. These cases require a high index of suspicion and appropriate diagnostic testing for proper management. In this report, we describe two patients with chronic lymphocytic leukemia who developed atypical presentations of herpes zoster and herpes simplex infections. Herpetic infections should always be in the differential diagnosis of cutaneous ulcerations with necrosis in patients who are immunocompromised. Because of the atypical appearance of the lesions, the diagnosis may be confused or mistaken for several other conditions.