A 65-year-old male presented with a right lower extremity venous ulcer. During workup, the patient was found to have extensive incompetence of the superficial and deep venous systems. This prompted evaluation for venous outflow obstruction. CT Venography showed compression of the proximal right external iliac vein at the right common iliac artery bifurcation between the external and internal iliac arteries. Treatment of the venous outflow obstruction resulted in near ulcer healing in 1 month. After correction of the superficial venous disease, the ulcer wholly healed. Extensive superficial and deep incompetence should prompt evaluation of the venous outflow in the pelvis.