Dural ectasia is a common finding in patients with Marfan syndrome, while many of these patients are on anticoagulants due to prosthetic heart valves. A 44-year-old man was transferred to the ER due to cauda equina syndrome. The patient was on warfarin. His CT scan revealed spontaneous hemorrhage in the lumbosacral region. The patient underwent an urgent laminectomy with subtotal removal of haemorrhagic tissue. Post-operatively, he developed sepsis due to wound leak. Additionally he developed resistance to heparin. The complications were successfully managed, and the patient was discharged 3 months after his admission. People with Marfan syndrome could have significant co-morbidities while their management can be complicated by various issues. We present a case of lumbosacral hemorrhage and cauda equina with the background of dural ectasia and anticoagulants and discuss the relevant set of complications and their management.