Esophageal perforations are rare but are associated with high morbidity and mortality. More than 50 percent of these are iatrogenic, largely due to instrumentation. Less frequent causes include Boerhaave's syndrome, foreign body ingestion, trauma, and malignancy. The highest incidences of perforation are at or near sites of narrowing, such as the cricopharyngeus muscle, the broncho-aortic constriction, and the gastroesophageal junction (GEJ). Primary surgical repair is recommended except in certain technically difficult scenarios or in the context of hemodynamic instability. Endoscopic repair via covered stents has shown success in case studies and retrospective reviews if there is control and drainage of extraluminal fluid collections. We present a case where endoscopic repair is utilized to treat a complicated perforation. The patient is a 67-year-old female who presented for Laparoscopic Nissen Fundoplication for a type IV hiatal hernia. An upper gastrointestinal (UGI) series on postoperative day 1 was normal but she had a fall on postoperative day 3. She was discharged home asymptomatic but returned a few days later for intractable vomiting, and was found to have a large intrathoracic fluid collection. Exploratory laparoscopy of the abdomen allowed for drainage of the collection and revealed a 3-4 mm esophageal perforation at the posterior aspect of the GEJ. An 8x123 mm fully-covered esophageal stent was placed over the site of perforation. This was upgraded to a 23x155 mm stent eight weeks later due to continued leak. Nevertheless, she continued to have esophageal leak. An endoscopy with a duodenoscope was performed. Using a ball-tip cannula, a fistula was cannulated over a 0.035-inch guidewire. A long fistula tract leading to multiple small fluid collections within a larger, loculated collection—measuring about 5 cm in total diameter—was found. A biliary double pigtail stent was placed into the main fistula tract to drain the fluid collections. On follow-up endoscopy, the pigtail stent was removed and there was resolution of these collections. An endoscopic clip was subsequently placed over the opening of the primary fistula. A new covered esophageal stent was placed over the clip to promote wound healing and closure. This stent was removed on follow-up endoscopy and no esophageal leak was seen. This case illustrates the ability of advanced endoscopic techniques to successfully treat esophageal leak with complex fistula formation.Figure: Placement of a guidewire within the main fistula, with smaller fistulae noted to be branching from it.Figure: Positioning a double pigtail biliary stent into the fluid collections of the smaller fistulae.Figure: Deployment of a covered esophageal stent atop the clip sealing the primary site of perforation.