Inferior vena cava (IVC) compression secondary to mass effect is accompanied by edema, ascites, back and abdominal pain, and central nervous system symptoms. Most IVC syndrome cases described in the literature focus on the focal treatment of IVC lesions, and reports of complete iliocaval reconstructions secondary to malignant IVC syndrome in the palliative context are limited. In this case report, we describe the clinical presentation, technical approach, and symptomatic outcomes of a patient with extensive malignant compression and invasion of the iliofemoral venous system. An 82-year-old male with metastatic lung cancer invading the right upper quadrant of the abdomen presented with scrotal and bilateral lower extremity edema, as well as anasarca. Computed tomography (CT) demonstrated an 11 cm right adrenal metastasis and extensive retroperitoneal lymphadenopathy resulting in the compression of the IVC and iliac veins. Femoral venography demonstrated extensive collateral venous pathway formation with the opacification of the para-lumbar and vertebral veins, in addition to the vertebral/sacral venous plexus. Iliocaval reconstruction was performed using venous-dedicated stents. This case report highlights a technically successful total iliocaval reconstruction in a complex palliative patient with diffuse metastatic disease resulting in IVC compression and syndrome.