A 90-year-old woman sustained a proximal esophageal perforation following transesophageal echocardiography. The perforation originated at the site of a Zenker's diverticulum and resulted in a false passage to the diaphragm. Initial management involved endoscopic placement of drains into the mediastinum in addition to bilateral chest drains and a gastrostomy. Following stabilization, the patient had repair of her Zenker's diverticulum and recovered uneventfully. We recommend that all procedures involving blind intubation of the esophagus should be preceded with specific pursuit of a background of cervical dysphagia.