Surgical resection is the consistent component of curative treatment strategies for primary malignant diseases of the stomach and the esophagus. The placement of anastomoses for the necessary reconstruction still accounts for substantial morbidity and in the case of a failure to rescue also for mortality, especially for esophagojejunostomy and esophagogastrostomy. The diagnostics of anastomotic leakage routinely involve computed tomography and endoscopy and timely performance appears to be essential. Endoscopy can simultaneously initiate the essential treatment step. A major reason for the improvement of postoperative outcomes after resection in the upper gastrointestinal tract in the last decades is the successful and mostly endoscopically performed management of anastomotic leakage, whereby different endoscopic treatment options are now available. Endoscopic vacuum therapy has become established as the standard, normally with an endoscopic vacuum sponge technique but is also now supplemented by a combination system of vacuum sponge and stent. Furthermore, a foil-coated multiple lumen nasogastric tube represents another available option, which can possibly especially be used as a prophylactic measure. The longest established endoscopic therapy option for anastomotic leaks, the endoluminal metal stent, has been replaced as the standard by the vacuum treatment but is still used in suitable situations. Additionally, there are endoscopic suture devices that are currently only used very occasionally. Surgical revision is always available as treatment escalation but is only recommended for very early occurrences and possibly technically related anastomotic leakage and in the case of failure of endoscopic treatment. This article describes and summarizes the diagnostics and treatment of anastomotic leakages after surgical procedures of the upper gastrointestinal tract.