Given the high volume of gastric bypass surgery done in the United States, surgeons are seeing increasing numbers of postoperative complications, many of which are diagnostic dilemmas. Surgeons are increasingly faced with patients with significant complaints and unclear etiology based on the available diagnostic tools. Surgical intervention, especially in the era of laparoscopic surgery is a powerful tool in making difficult diagnoses, and strong clinical suspicion is the sole indication in these cases. We present two such cases and the operative findings and treatments. The first case is a patient who complained of worsening abdominal pain usually after meals 4 months post op from a lap. gastric bypass. Preoperative evaluation was unrevealing. The video demonstrates findings of significant adhesions with a narrowing at the jejunojejunostomy which is treated with revision and adhesiolysis. The second case is a patient who had undergone vertical banded gastroplasty 10 years ago with failure of the staple line. She underwent a successful laparoscopic conversion to a RY gastric bypass three months prior with abdominal pain for the past 2 months. Diagnostic evaluation included a negative Endoscopy, CT scan and UGI series. The video sequence reveals a Petersen's hernia. These two cases highlight the wide range of intraoperative findings of complications after laparoscopic gastric bypass surgery, especially the importance of clinical suspicion and early intervention when faced with a diagnostic dilemma.