Over 80% of patients undergoing bariatric surgery are women, approximately half of whom are of reproductive age. The most common procedure in the United States is the Roux-en-Y gastric bypass. Small bowel obstruction is one of many recognized postoperative complications. For such a serious condition, this entity presents with remarkable subtlety and is easily misdiagnosed, particularly in pregnant women. The consequences of late recognition can be life-threatening to both mother and fetus. We aim to decrease preventable maternal and perinatal morbidity and mortality by revealing diagnostic and therapeutic missteps related to Roux-en-Y gastric bypass-associated small bowel obstruction.