Objective: Esophageal perforation (EP) is a fatal status that continues to be challenging the management, with the incidence of mortality and morbidity has been reported to reach 40%. Its diagnosis may be tricky as it usually presents with a wide range of non-specific symptoms. Our study aims to report characteristics, relay our experience with EP management, and evaluate the various strategies used. Methods: This study retrospectively evaluated the management of 53 patients with EP over 13 years. The confirmed diagnosis was established by esophagogram with water-soluble contrast, contrast-enhanced computed tomography, and esophagus-gastro-duodenoscopy. Initial management was categorized as conservation, endoscopic stent, or surgery. Re-intervention and different outcomes were recorded and analyzed. Results: Thoracic EP is the most common location (71.7%). The most common cause of EP was iatrogenic (35.8%). About 58.5% of patients were diagnosed ≤ 24 hours. The mean Pittsburg severity score was 7.5. The initial management was conservation (35.8%), an endoscopic stent (17%), and surgical intervention (47.2%). ICU and organ support were needed in 35.8% and 20.8%, respectively. The mean hospital stay for all patients was 27.7 days. Morbidity and mortality were recorded at 30.2% and 18.9%, respectively. Conclusion: EP management should be flexible with a tailored strategy for every patient. Etiology, site, severity score, time to management, and patient reserve are significant factors in management and prognosis.