Purpose: Chylous ascites is a rare sequela of small bowel volvulus, with most cases arising due to malignancy, trauma or cirrhosis. Thoracic duct ligation during oesophagectomy can result in lymphatic changes which may increase a patient’s vulnerability to chyle leakage in the setting of an acute bowel obstruction. This report describes chylous ascites associated with midgut volvulus in a post-oesophagectomy patient and highlights potential pathophysiological mechanisms and operative considerations. Methodology: A man in his 60s presented with acute abdominal pain and nausea. His medical history included an Ivor Lewis oesophagectomy with thoracic duct ligation three years earlier for oesophageal adenocarcinoma. Laboratory investigations revealed an elevated white cell count (13.2 x109/L) and lactate 2.2 mmol/L. Contrast-enhanced CT revealed swirling of the mesenteric vessels with venous engorgement and reduced small bowel attenuation, suggestive of a midgut volvulus, and reduced enhancement concerning for bowel ischaemia. The patient’s symptoms and lactate normalised on serial review, with the volvulus thought to have spontaneously resolved. Results: Diagnostic laparoscopy revealed over 600 mL of milky intraperitoneal fluid without bowel necrosis. A band adhesion was identified as the lead point of an intermittent volvulus and was divided. Fluid analysis confirmed chylous ascites with elevated triglyceride levels (10.36 mmol/L), with negative cultures and no malignant cells on cytology. The patient’s postoperative course was uneventful. Conclusion: Prior thoracic duct ligation may predispose patients to chyle leakage in the setting of acute bowel obstruction. Chronic lymphatic remodelling following thoracic duct ligation can lead to the development of fragile collateral vessels that are vulnerable to rupture when lymphatic outflow is acutely occluded. Recognition of prior surgical interventions is therefore important in guiding intraoperative decision-making.