Inferior vena cava filter (IVCF) placement is indicated in patients with acute venous thromboembolism who cannot be adequately anticoagulated or have failed anticoagulation. Prompt IVCF retrieval decreases the risk of complications associated with longer dwell times including fracture, penetration, and further thromboembolic events. Endovascular IVCF retrieval has been performed despite penetration into adjacent structures including the aorta; however, penetration into the false lumen of an aortic dissection is rarely seen. This case report describes endovascular management of an 11 year old IVCF that caused iliocaval thrombosis and penetrated the false lumen of a chronic type B aortic dissection.