Bariatric surgery is an effective treatment for morbid obesity, but procedures like sleeve gastrectomy may lead to complications, including gastroesophageal reflux disease (GERD), esophageal motility disorders, and hiatal hernia. These complications can be particularly challenging in patients requiring long-term pancreatic surveillance, such as those with intraductal papillary mucinous neoplasms (IPMN), where preserving gastric continuity is essential for endoscopic access. This report presents a case of a 64-year old woman with a history of laparoscopic sleeve gastrectomy who developed severe GERD, dysphagia, and postprandial chest pain. Diagnostic workup revealed a large hiatal hernia, gastric sleeve stenosis, and a proximal esophageal diverticulum. Given the complexity of her altered anatomy and need for continued IPMN surveillance, a robotic surgical approach was employed. The patient underwent successful robotic hiatal hernia repair with resection of an 8 cm intrathoracic esophageal diverticulum. Postoperative recovery was uneventful, and she remained symptom-free at 1-year follow-up. This case highlights the value of a robotic approach in managing complex post-bariatric complications while preserving access for essential diagnostic surveillance.