Phlegmasia cerulea dolens (PCD) is an uncommon but potentially limb-threatening complication of acute deep vein thrombosis. A 56-year-old male presented with PCD. Color Doppler ultrasonography revealed extensive thrombosis of the left superficial and common femoral and external and common iliac veins. After an unsuccessful iliofemoral thrombectomy, contrast-enhanced computed tomography revealed iliofemoral deep vein thrombosis due to May–Thurner syndrome (MTS). After the deployment of an inferior vena cava filter, the thrombotic occlusion was traversed with a guidewire and direct stenting was performed to achieve immediate recanalization. The patient was discharged two days after the procedure, demonstrating significant clinical improvement. MTS is a rare cause of PCD. Direct iliac vein stenting may be a safe and effective alternative treatment for rapid recanalization if percutaneous mechanical thrombectomy devices are unavailable.