Chronologically, complications can be classified as intraoperative, early, and late. The authors analyze complications according to this classification on the basis of more than 400 esophageal operations and related literary data. As regards intraoperative complications, they deal only with those occurring at transhiatal esophagectomy (e.g., tracheal tear, bleeding, pneumothorax, laryngeal nerve injury). Among the early complications, they survey the incidence of transplant necrosis and related mortality, further sequelae ensuing from subacute ischemia of the replaced organ and analyze in detail the questions which arise regarding anastomotic leakage. Firstly, they deal with those causative factors that influence the frequency of anastomotic insufficiency, such as the technical "know-how" of anastomosis making (e.g., one layer vs two layers; stapling or manual suture; interrupted or running suture), the way of replacement using whole stomach or tube-stomach and the consequences originating from the route of replacement (e.g., anterior or posterior mediastinal route). Incidence and management of chylothorax are also dealt with. While dealing with late complications, the authors give a detailed comment on anastomotic strictures and also other factors facilitating the development of late dysphagia, such as peptic stricture and tumor of the organ remnant. Finally, some cases successfully treated by surgery are presented (skin-tube formation in cases following transplant necrosis; abolition of a pharyngogastric anastomosis stricture using a free jejunal transplant and surgical solution of an anastomotic stricture from median sternotomy approach).