This paper aim is to discuss the main etiopathogenic aspects responsible for eso-digestive anastomotic leakage, as well as prophylactic and therapeutic measures of this postoperative complication. There were studied 173 consecutive eso-digestive anastomosis: 103 anastomosis performed for malignancy and 70 anastomosis for benign conditions. Surgical operations followed by an eso-digestive anastomosis were: esophageal reconstruction for benign esophageal caustic strictures (n=67); total gastrectomy (n=55); total esophagectomy (n=13); total esophagectomy plus total gastrectomy (one case); eso-gastrectomies (n=34); upper gastric pole resection (n=2); distal esophageal resection (n=1). Eso-digestive anastomosis topography were cervical (n=81), intrathoracic (n=37) and abdominal (n=57). There were 30 eso-gastrostomies, 81 eso-jejunostomies, and 62 eso-colostomies. There were recorded 24 eso-digestive anastomotic dehiscences (13.8%): 14 in the cervical region (17.2% out of 81 cervical anastomosis); 5 intrathoracic leakages (14.2% out of 35 anastomosis); 5 intraabdominal anastomotic dehiscences (8.7% out of 57 intraabdominal anastomosis). Four patients died as an anastomotic leakage consequence: two patients died after cervical eso-gastrostomy dehiscences, one patient died after an intrathoracic eso-jejunostomy leakage, and one patient died after intraabdominal eso-gastrostomy leakage. In conclusion, we analyze postoperative results, emphasizing the role of discovering and removal of predisposing factors which may lead to an eso-digestive anastomotic leakage.