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Purpose: Relief of gastric outlet and distal biliary obstruction may be accomplished by open surgery or by minimally invasive techniques including endoscopic and laparoscopic approaches. We examined the feasibility and safety of laparoscopic gastric and biliary bypass in all patients with malignant and benign disease requiring surgical relief of obstructive symptoms., Materials and Methods: Patients with benign duodenal stricture or inoperable malignancy underwent therapeutic laparoscopic bypass surgery. Prophylactic gastric or biliary bypass was added in selected patients with nonmetastatic malignancy., Results: Twenty-eight patients (17 of them female) with a median age of 67 years (range, 26-81 years) underwent 29 laparoscopic bypass procedures for malignant (n = 23) or benign (n = 6) disease. One patient who underwent a Roux-en-Y gastrojejunostomy for non-steroidal anti-inflammatory drug induced ulcer disease developed stenosis of the stoma that required laparoscopic refashioning 2 months later, accounting for the 29th procedure reported herein in 28 patients. Surgery included the construction of a single gastric (n = 16) or biliary (n = 5) bypass or a double bypass (n = 8), and an additional prophylactic bypass in 5 of 23 cancer patients (21.8%). All procedures were completed laparoscopically. The median operative time was 90 minutes (range, 60-153 minutes) and mean postoperative hospital stay was 4 days (range, 3-6 days). Complications developed following 4 procedures (13.8%) and 1 patient died (3.4%). No complications occurred in patients with prophylactic bypass. One patient required laparoscopic revision of the gastroenterostomy 2 months postoperatively, for benign disease. No recurrence of obstructive symptoms was observed in cancer patients during follow-up., Conclusion: Laparoscopic bypass surgery for distal biliary and gastric obstruction in patients with benign or malignant disease results in low morbidity and mortality and short postoperative hospital stay. The addition of prophylactic bypass in patients with nonmetastatic unresectable malignancy appears safe and effective.