Candy cane syndrome is an underappreciated complication reported in bariatric patients following Roux-en-Y gastric bypass. It results from an excessively long blind afferent Roux limb at the gastrojejunostomy that can lead to food accumulation. Patients often present with nausea, vomiting, food intolerance, acid reflux, and abdominal pain. Many patients remain undiagnosed due to vague gastrointestinal symptoms, delayed presentation, and physician unawareness. Here, we present the case of a 40-year-old female who presented for a third opinion on the cause of intractable acid reflux and nausea. Workup revealed her symptoms stemmed from an excessively long afferent Roux limb. Traditionally, treatment would include laparoscopic or open surgical removal of the blind limb. Although effective, surgical intervention is invasive, may not be an option in high-risk patients, and can lead to further complications. We were able to successfully address this patient’s candy cane syndrome by utilizing a novel endoscopic approach to revise the gastrojejunal anastomosis, which led to full resolution of her symptoms. Endoscopic therapy of candy cane syndrome may provide a minimally invasive approach that exposes patients to decreased procedural risk while potentially producing similar treatment results as more invasive surgical approaches.