Esophageal perforation is a serious condition with a high mortality rate. Successful therapy depends on the size of the rupture, the time elapsed between rupture and diagnosis, and the underlying health of the patient. Common causes of esophageal perforation include medical instrumentation, foreign-body ingestion, and trauma. A case of esophageal perforation due to fish bone ingestion in a 70-year-old diabetic male is described here, with a review of the pertinent literature. The patient presented with odynophagia after a meal that included fish. Initial evaluation was nondiagnostic and the patient was discharged home. The patient returned 12 days later with fever, generalized weakness, and persistent dysphagia. Esophageal biopsy of a necrotic ulcer revealed foreign material with acute inflammatory changes. Computed tomography scan demonstrated a pneumomediastinum. The patient became hemodynamically unstable and died on the third hospital day.