The endoscopic management of four selected patients with inveterate esophageal perforations or leaks is presented. One patient had a perforation of the cervical esophagus following endoscopic removal of a foreign body already treated with surgical drainage; two patients had a leak following diverticulectomy and esophagogastrostomy, respectively, persistent after multiple surgical repairs; the last patient had a spontaneous perforation of the thoracic esophagus persistent after two transthoracic repairs. The mean time elapsed between the diagnosis of perforation and the endoscopic treatment was 19 days. In one patient, transesophageal drainage of a mediastinal abscess was performed. In the other three patients, a stent was placed to seal the leak in combination with gastric and esophageal aspiration. Two of these patients underwent endoscopy in critical condition and could have not been candidates for major surgical procedures. All patients received enteral nutrition. No morbidity or mortality related to the endoscopic procedure was recorded; the treatment was effective in all patients who recovered and resumed oral feeding within 3 weeks. We conclude that endoscopic transesophageal drainage and stenting are effective procedures in the management of patients with inveterate esophageal perforations or leaks.