Anastomotic fistulas remain one of the most severe complications following esophageal and gastric cancer surgery, significantly impacting morbidity and mortality rates. Materials and methods: This retrospective study evaluates the risk factors associated with anastomotic fistula formation and assesses the efficacy and complications of esophageal stenting as a treatment modality. Data from 110 patients treated at the Surgery Clinic of "Sf. Maria" Hospital in Bucharest, between 2019 and 2023 were analyzed. The study population was divided into two groups: patients with postoperative anastomotic fistulas who underwent endoscopic esophageal stenting and those who did not develop fistulas. Results: Key findings indicate that advanced age, smoking, alcohol consumption, tumor size, TNM stage, hypertension, diabetes, and preoperative radiotherapy were significantly associated with an increased risk of fistula formation. Additionally, hypoalbuminemia, anemia, and impaired renal function emerged as critical predictors. While esophageal stenting proved to be an effective intervention, it was associated with specific complications requiring careful patient selection and monitoring. Conclusions: This study identifies multiple risk factors associated with the development of anastomotic fistulas after esophageal and gastric cancer surgery. Understanding these risk factors is crucial for identifying high-risk patients and implementing targeted perioperative strategies to improve surgical outcomes and reduce postoperative complications.