Port site hernias are a rare complication following robotic surgery that can result in disastrous outcomes. We describe incarcerated port site hernias in two patients with obesity. Both patients required laparoscopic reduction. Following laparoscopic reduction, one patient's postoperative course was complicated by pneumatosis intestinalis, requiring exploratory laparotomy and subsequent small bowel resection. It is standard practice to not close the fascia of port sites less than 12 mm in robotic surgery. However, this allows for the rare possibility of small bowel herniation through the port site. We suggest that our patients' history of obesity and metabolic dysfunction contributed to difficult port retention during the case, and longer operating times which caused an increased amount of torque at the port site. Additionally, compared with laparoscopic surgery, robotic surgery is associated with increased torque at port sites. The combination of these risk factors extended the fascial defect, ultimately leading to the incarceration of small bowel in the port site.