Progressive esophageal carcinoma can infiltrate the surrounding tissues with subsequent development of a fistula, most commonly between the esophagus and the respiratory tract. The endoscopic placement of covered self-expanding metallic stents (SEMS) is the treatment of choice for malignant esophageal fistulas and should be performed immediately, as a fistula formation represents a potential life-threatening complication. We report the case of a 64-year-old male diagnosed with esophageal carcinoma, who had a 20Fr surgical gastrostomy tube inserted before chemo- and radiotherapy and was referred to our department for complete dysphagia, cough after swallowing and fever. The attempt to insert a SEMS using the classic endoscopic procedure failed. Then, a fully covered stent was inserted, as the 0.035” guide wire was passed through stenosis retrogradely by using an Olympus Exera II GIF-N180 (4.9 mm in diameter endoscope) via surgical gastrostomy, with a good outcome for the patient. The retrograde approach via gastrostomy under endoscopic/fluoroscopic guidance with the placement of a fully covered SEMS proved to be the technique of choice, in a patient with malignant esophageal fistula in whom other methods of treatment were not feasible.