May-Thurner syndrome (MTS) also termed iliocaval compression or Cockett-Thomas syndrome is a common, although rarely diagnosed, condition in which the patient has an anatomical variant wherein the right common iliac artery overlies and compresses the left common iliac vein against the fifth lumbar spine resulting in increased risk of iliofemoral deep venous thrombosis. This variant has been shown to be present in over 23% of the population but most go undetected. We present a patient with MTS who developed high output cardiac failure due to an iatrogenic iliac fistula. The patient underwent an extensive workup for a left to right shunt including MRI and arterial duplex in the vascular lab. He was ultimately found to have a 2.1 cm left common iliac artery aneurysm and history of common iliac stent. We took the patient to the operating room for aortogram with placement of an endovascular plug of the left internal iliac artery and aorto-bi-iliac stent graft placement with CO2 and IV contrast. Subsequently the patient underwent successful stent placement in the area that was compressed followed by 6 mo of anticoagulation with warfarin. The flow from the fistula decreased significantly.