Postoperative intraperitoneal or ectopic free air may occur after abdominal surgery, gynecologic surgery, laparoscopic surgery, or endoscopic procedures and, in rare cases, represent gastrointestinal perforation, requiring emergency laparotomy. Evaluating patients with postoperative signs of bowel perforation may be difficult, especially when day-case laparoscopic or endoscopic surgery is performed, with the patient readily discharged from hospital. Delayed diagnosis of gastrointestinal perforation due to underestimation of postoperative free air is associated with a high morbidity and mortality rate. We report two cases of patients presenting with postoperative free air along with the clinical presentation and management.