Herpes zoster along the maxillary division of the trigeminal nerve is a rare condition that is caused by reactivation of the varicella zoster virus that resides within the trigeminal ganglion after the primary infection of chickenpox. The disease may be manifested as a toothache during its prodromal stage. The active stage of the disease is characterized by the appearance of a vesicular rash. Postherpetic neuralgia is a common complication of herpes zoster after resolution of the facial and intraoral symptoms. There is increasing evidence for herpes zoster patients to develop stroke later in life. The present case reports the development of herpes zoster maxillaris in a 71-year-old man whose maxillary right canine was diagnosed as pulpal necrosis and symptomatic apical periodontitis and was subsequently treated endodontically by cleaning and shaping and filling the canal space with gutta-percha and an epoxy resin–based sealer. The patient presented 3 days later with midfacial ulceration, desquamation, and crusting as well as intraoral ulceration along the course of the V2 dermatome. After successful treatment with antiviral medication, postherpetic neuralgia developed within the next 2 months. Complete resolution of the neuralgia occurred at the 4-month recall with negligible facial scarring. Herpes zoster may mimic odontogenic pain during the prodromal stage of the disease. Reactivation of the virus has also been implicated in the pathogenesis of pulpal pathoses. These paradoxical facets are of interest to the endodontist and should be considered in the differential diagnosis of the disease.