Severe venous dysfunction in the setting of subacute iliocaval occlusion is a high cause of morbidity and mortality in patients. Fortunately, the development of the appropriate interventional management has allowed for better patient prognosis, despite device limitations. Severe cases of venous insufficiency, anatomically challenging vasculature, and device failure remain imperative when discussing the caveats for interventional success. The current gold standard of treatment for iliocaval disease has proven to be venoplasty in conjunction with stent placement within thrombotic occlusive areas. Though intuitive for modern day interventionists, this standard is not always forthright, especially when the most prevailing interventions fail to adequately treat certain venous pathologies. In this case, interventional operators must be willing to adapt their technical proficiency and knowledge of readily available devices to successfully treat the progressive nature of venous insufficiency. The following report demonstrates an example of how an interventional operator acclimated their interventional approach to successfully treat a severe and technically challenging case of subacute iliocaval occlusion, using an aortic endograft. In this first documented deployment of an aortic endograft in an iliocaval confluence, the results show resolution of the patient’s subacute iliocaval occlusive disease, as well as complete iliocaval patency and the absence of post-procedural complications.