Abstract Background Benign Tracheoesophageal fistula (TOF) caused by foreign body impaction is a rare condition requiring technical expertise. There are choices available based on the individual patient's situation, including endoscopic management, local resection and defect closure, and, in rare cases, esophagectomy. Methods A 58-year-old male had a history of artificial tooth dislodgement that got impacted in the esophagus, resulting in dysphagia. Endoscopy showed an impacted denture with an underlying transmural esophageal perforation, closed with clips and an endoloop. Two weeks later, partially covered SEMS was placed. Failure to retrieve the SEMS after repeated attempts due to tissue ingrowths, he was referred for management. CECT showed a stent in situ with a small air-filled cavity left lateral to the tracheal bifurcation. Bronchoscopy revealed the compression of the posterior tracheal wall and the presence of an endoclip in the posterior wall of the left main bronchus (LMB). Results The patient was planned for a two-stage operation. In the first stage, esophagus was mobilized along with the stent and the fistulous tract was excised. The esophagus was divided at both ends in the thorax. Up to this part, the procedure was done with single-port VATS without CO2 and in the left semi-prone position with a bronchial blocker in the right main bronchus. The fistula with the LMB was closed with an intercostal muscle flap and a bovine pericardial patch with transient apnoea. During this part, we extended the incision in the fourth space to raise the flap. Cervical esophagostomy was matured, and a feeding jejunostomy was created. The postoperative phase was uneventful, and he was discharged on the 5th postoperative day. After 4 weeks, we did the second phase of surgery, where we made a 4 cm retrosternal gastric conduit and performed the hand-sewn anastomosis with the cervical esophagus, which was taken down from the skin. The patient had an uneventful postoperative course and was allowed to be taken orally on day five and discharged subsequently two days later. Conclusions TOF demands a multidisciplinary treatment strategy. Successful outcomes are determined by patient triage, delineation of the location and size of the defect, mediastinal contamination, and the availability of expertise.