A 62-year-old white male presented with recurrent pulmonary embolism (PE) despite having an inferior vena cava (IVC) filter. Investigations ruled out upper limb deep vein thrombosis (DVT) and IVC thrombus, the common causes for a PE in the presence of IVC filter. The culprit was double IVC with a persisting left supracardinal vein that allowed an alternate route for the leg DVT to cause PE. IVC anomalies have a propensity to cause lower limb DVT. Although rarely suspected recent studies have revealed that IVC anomalies are not rare if anticipated and evaluated. Chest CT scans in cases of suspected idiopathic PE should extend up to the renal veins as this will identify common IVC anomalies. Therapy to prevent recurrent DVT can be instituted. A good quality venacavagram should always precede any IVC filter placement as this will identify almost all IVC anomalies and appropriate steps can prevent a recurrent PE.