Laparoscopic sleeve gastrectomy (SG) is a widely performed bariatric procedure known for its safety and efficacy, yet complications, particularly postoperative leaks, remain a concern. Endoscopic stenting is one of the approaches for leak management that has some complications such as the rare fistula with adjacent organs. Here, we present a unique case of a 56-year-old diabetic female who developed a gastroenteric fistula following endoscopic stent placement for a post-SG leak. The patient had a delayed stent removal, and three weeks later she presented with dysphagia and vomiting in a follow-up appointment. Esophagogastroduodenoscopy (EGD) showed an esophageal stricture and a large gastroenteric fistula that was confirmed by imaging to be a fistula between the pylorus and proximal small bowel. The patient's symptoms improved gradually with conservative management, and imaging showed the resolution of the fistula and associated esophageal stricture. This case highlights the importance of timely stent removal (ideally within 6-8 weeks) and close follow-up with EGD and CT to detect and manage potential complications, while emphasizing the need for further research on optimal stent placement duration.