Complete esophageal stenosis secondary to peptic stricture in the upper esophagus is rare. It is, however, a serious medical problem that may require otolaryngologic intervention because of life-threatening dysphagia and weight loss. We report the case of an elderly patient who presented with an upper esophageal stricture, without the typical symptoms of gastroesophageal reflux disease, that progressed to complete esophageal obstruction despite use of proton pump inhibitors and esophageal dilatation. Definitive management of this difficult problem required esophagectomy and gastric pull-up. We discuss the pathophysiology, clinical presentation, differential diagnosis, and multidisciplinary management of peptic esophageal strictures. This case illustrates the difficulty in managing high peptic strictures.