KlippelTrenaunay Syndrome (KTS) is a rare congenital nonhereditary syndrome of vascular malformations and soft tissue and bone hypertrophy. Though the involvement of gastrointestinal tract (GI) is uncommon in KTS, it can be a source of life–threatening bleed with a high morbidity and mortality rates. We here report a case of a 26 year old gentleman, already a diagnosed case of KTS, who presented to us with recurrent GI bleed and anaemia necessitating blood transfusions every 20 days. This case report aims to highlight the management protocols for this rare presentation of the syndrome.