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Chilaiditi syndrome is a very rare disorder characterized by abdominal pain due to the entrapment of the colon between the liver and the diaphragm. However, it is rare to have bowel perforation as a complication of this syndrome with only 2 cases reported to date. In this article, we present the case of a 56-year-old woman with medical history of scleroderma who presents with abdominal pain and was found to have colonic perforation from Chilaiditi syndrome. She was also incidentally found to have cecal adenocarcinoma. Sometimes abdominal pain in patients with Chilaiditi syndrome may be more than benign and calls for increased attention from clinicians regarding this.