Anastomotic leaks are still among the most common severe postoperative complications and account for the majority of postoperative deaths after esophagectomy and gastrectomy. Every disturbance of the normal postoperative course should trigger surgeons to consider an underlying anastomotic leak and initiate a specific diagnostic workup. This includes direct endoscopic inspection of the anastomosis to evaluate the vitality of the anastomosed organs and the size of the leak. Adequate external drainage of the leak and prevention of further contamination are the primary therapeutic goals. Selection of therapy is guided by the available modalities for sufficiently draining the leak and avoiding sepsis. The spectrum of therapeutic options ranges from simple opening of the neck incision in cervical esophageal anastomoses, interventional placement of drains, to endoscopic intervention with closure of the fistula or placement of stents, and reoperation with exclusion, diversion, or discontinuity resection.