Sudden onset of dysphagia due to a gastric bezoar migrating to the esophagus is a relatively rare condition. A 72-year-old male patient with known gastric bezoar presented with sudden difficulty swallowing following nausea and vomiting caused by adhesive ileus. Gastroscopic examination showed a bezoar and associated compression ulcers in the esophagus. The bezoar was pushed towards the stomach and extracted by successful endoscopic fragmentation.