A 51-year old Caucasian female had presented with intractable Gastroesophageal Reflux Disease (GERD), chronic dysphagia and food intolerance over a period of 6 years following a sleeve gastrectomy. With conservative management options having failed she underwent a Revisional Roux-en-Y gastric bypass. Although the patient did well initially, she developed dysphagia once again with her BMI falling to 17.7 (initial BMI 44.6). Upper endoscopy showed a patent anastomosis but with a stricture in the roux limb and an ulcer distal to that stricture with no marginal ulceration at the anastomosis itself. Workup resulted in increased suspicion for carcinoid tumor and Inflammatory Bowel Disease (IBD) due to elevated chromogranin A, Single Photon Emission Computed Tomography (SPECT) study and elevated fecal calprotectin respectively. Final pathology of the stricture was positive for gastric mucosa which was subsequently excised. Two months later, abdominal pain and signs of dehydration led to a small bowel series X-ray with barium showing high suspicion for Crohn's disease.