Abstract Background Esophagectomy is needed for a variety of esophageal disorders, the most common indication is cancer esophagus, however, it is needed in benign disorders as postcorrosive strictures & endstage achalasia with esophageal dilatation. Anastomotic leakage is one of the most severe complications leading to significant morbidity and increased risk of mortality. Objective To evaluate different approaches in management of leakage after gastroesophageal anastomosis in Upper GIT surgery unit in Ain Shams University Hospitals. Patients and Methods This study was conducted at General surgery department, Ain Shams University Hospitals. Approval of the Ethical Committee was obtained. The study was conducted over patients with postoperative gastroesophageal leakage during the period from 3/2019 to 3/2021. Results Patients managed after cervical anastomosis leakage needed less time to start oral intake& had shorter hospital stay in comparison to those managed after thoracic leakage. There was a higher perioperative morbidity and mortality in patients who underwent surgical intervention as compared with patients who underwent conservative treatment. Conclusion Anastomotic leak after surgery for esophageal diseases can vary in location, onset time, size, and extent. For local management, personalized treatment should be decided based on patient’s particular situations. Cervical anastomosis leakage has less morbidity & mortality compared to thoracic anastomosis. Conservative treatment is safe and successful in many cases, in cervical leakage conservative management is effective in most cases. Stent implantation is an effective method with other emerging endoscopic techniques. Resurgery should be considered carefully and reserved to uncontrolled leakage or patients with failed conservative management.