Esophagectomy is the mainstay for treating esophageal cancers and other pathology. Even with refinements in surgical techniques and the introduction of minimally invasive approaches, the overall morbidity remains formidable. Complications, if not quickly recognized, can lead to significant long-term sequelae and even death. Vigilance with a high degree of suspicion remains the surgeon’s greatest ally when caring for a patient who has recently undergone an esophagectomy. In this review, we highlight different approaches in dealing with anastomotic leaks, chyle leaks, cardiopulmonary complications, and later functional issues after esophagectomy.