May-Thurner syndrome is a rarely diagnosed condition in which patients develop iliofemoral deep venous thrombosis (DVT) due to an anatomical variant in which the right common iliac artery overlies and compresses the left common iliac vein against the lumbar spine. This variant has been shown to be present in over 20% of the population; however, it is rarely considered in the differential diagnosis of DVT, particularly in patients with other risk factors. Systemic anticoagulation alone is insufficient treatment, and a more aggressive approach is necessary to prevent recurrent DVT. Herein, we present a patient with multiple risk factors for DVT. With a comprehensive diagnostic approach, she was found to have May-Thurner syndrome. Local infusion of thrombolytics as well as mechanical thrombectomy failed to resolve the thrombus. Subsequently the patient underwent successful stent placement in the area that was compressed followed by 6 months of chronic anticoagulation with warfarin. There has been no recurrence of DVT in the ensuing 18 months.