Over-the-Scope Clip system, also called “Bear Claw,” is a novel endoscopic modality used for closure of gastrointestinal defect with high efficacy and safety. We present a patient with history of eosinophilic gastroenteritis and multiple abdominal surgeries including Billroth II gastrectomy complicated by a large chronic duodenocutaneous fistula from a Billroth II afferent limb to the abdominal wall. Bear Claw clip was used for closure of this fistula. The patient developed acute cholangitis one day after placement of the Bear Claw clip. Acute cholangitis due to papillary obstruction is a potential complication of Bear Claw placement at the dome of the duodenal stump (afferent limb) in patient with Billroth II surgery due to its close proximity to the major papilla.