Herpes simplex virus (HSV) esophagitis and duodenitis are well-known features of herpes virus reactivation in immunosuppressed patients. We discuss the case of HSV esophagitis concomitant with duodenitis in an immunocompetent individual. A 77-year-old male patient, previously healthy, was found to have on upper endoscopy several ulcers in the esophagus and second portion of the duodenum. A diagnosis of HSV esophagitis concomitant with duodenitis was made. The patient was started on intravenous acyclovir, and 48 hours after treatment, his symptoms significantly improved. He was then discharged on acyclovir per os for a total of 14 days. Endoscopy 1 month later showed complete resolution of both esophageal and duodenal ulcers. Physicians should keep the diagnosis of HSV esophagitis with duodenitis in the differentials in the setting of odynophagia, dysphagia, and epigastric pain, even in the case of an immunocompetent individual. Further research is needed to strengthen the literature on this topic.