Malignant bowel obstruction is one of the toughest clinical challenges in gynecology. Few rigorous clinical trials exist to guide management.While conservative options should be exhausted first, palliative bowel surgery remains the only approach offering the possibility of quality time, restoration of oral nutrition, and on-going cancer-directed therapy. The capacity to address malignant bowel obstruction becomes ever more critical as many of the most promising new treatments for gynecologic malignancy are targeted biologic oral agents. The best candidates for surgery are obstructed in a single location, naive to prior bowel obstruction surgery, have treatment options remaining, and have minimal ascites or carcinomatosis. Postoperative 30-day mortality after palliative bowel surgery ranges from 4–40% and perioperative morbidity including postoperative pain, bowel leaks, abscess, sepsis are high, range from 5–86%.Thus, the choice to proceed with surgery requires exceptional doctor–patient communication, a highly skilled surgical team, and meticulous patient selection.