Patient is a 63 year-old male with history of morbid obesity (BMI 42), type II diabetes, and high cholesterol, who underwent a single anastomosis duodeno-ileal bypass with sleeve gastrectomy (SIPS/SADI-S). This was complicated by recurrent obstruction at the duodeno-ileal anastomosis, difficulty with diet advancement beyond clear liquid, subsequent severe malnutrition and resulting rapid weight loss. A diagnostic laparoscopy demonstrated that adhesions were tethering the stomach and exacerbating the kink at the angularis. Lysis of these adhesions resulted in marked straightening of this area. He had much better PO tolerance for the first three months after this procedure but once again his symptoms returned. A 3D reconstruction from a CT scan done at this time demonstrated the recurrence of the kinking and narrowing of the sleeve at the angularis. Given persistent poor oral intake due to above, decision was made to convert his SIPS to a gastric bypass. Meticulous lysis of adhesions was performed. An intraoperative endoscopy revealed significant relief of the obstruction at the level of the anastomosis. A Braun enteroenterostomy was done, and the duodenoileostomy was taken down. A retrocolic Roux-en-Y gastric bypass, with a 100 cm Roux limb was performed. Three months post gastric bypass, the patient was tolerating solid foods and drinking liquids without difficulties. His weight stabilized and his comorbidities remained in remission.