A 50 year old female with recent sleeve gastrectomy presented with 24-hours of severe abdominal pain. Her vital signs and labs were grossly normal; however CT demonstrated inflammatory changes to her stomach and abdomen likely secondary to perforation. The patient underwent emergent diagnostic laparoscopy where the staple line was examined with no obvious leak, gastric fistula, or abscess. An endoscopic provocative air leak test was performed with no evidence of leak. Due to high clinical suspicion, an upper GI series was obtained and demonstrated focal contrast leak from the gastric cardia. The patient underwent repeat endoscopy where a dimple with surrounding granulation tissue was noted on the proximal end of the sleeve, distal to the gastroesophageal junction. An OverStitch device was used to approximate the tissue followed by deployment of a 23mm x 15.5cm WallFlex endoprosthesis. A repeat upper GI study was negative and the remainder of her hospital course was uncomplicated. Sleeve gastrectomy is associated with three significant complications: staple line bleeding, leak, and stricture. Staple line leaks are among the most concerning with significant morbidity and mortality if left untreated. There remains an absence of an internationally adopted algorithm for the management of leaks. Once diagnosed, treatment of a leak often depends on the clinical status of the patient and may range from surgical intervention in an unstable patient, to endoscopic exclusion techniques, and conservative management. This case report also emphasizes the importance of utilizing an upper GI series to more accurately characterize a leak.