Esophageal anastomotic fistula (AF) is a frequent and severe complication of an esophagectomy due to esophageal or eso-gastric junction cancer, regardless of the selected surgical technique. AF is usually treated by endoscopic stent placement. Objectives: This study aims to examine the efficacy of stents in the treatment of AF, analyzing the healing period and the factors that contribute to its delay. Methods: We collected data from 55 patients who underwent stent implantation for AF, and analyzed multiple variables related to patient healing time and surgical technique with two primary endpoints: post-stenting hospital stay and the time of stent usage until fistula closure. The patients were divided into three groups based on the anastomosis type (eso-gastric anastomosis, eso-gastric cervical anastomosis and eso-jejunal anastomosis) and they were compared using the primary endpoints. Results: Our findings show the differences between the three groups, with a longer hospital stay for eso-gastric anastomosis, and an extended time of fistula closure in the case of eso-gastric cervical anastomosis. We also found a significant correlation between the size of the fistula and the hospital stay (R = 0.4, p < 0.01). Regarding patients' risk factors, our results show an extended post-stenting hospital stay for those patients that underwent preoperative radiotherapy. Conclusions: Our results offer an extended view of the efficiency, hospitalization duration and healing time for esophageal anastomotic fistula, and reveal some of the factors that interfere with its resolution.