Background: Complex congenital anomalies of the inferior vena cava (IVC) are rare sequelae of inappropriate persistence or regression of embryological precursor veins. These anomalies are typically asymptomatic and generally do not warrant intervention. Case Presentation: Here we present a case of severely symptomatic left IVC with infrahepatic disruption, azygos continuation, and retroaortic left renal vein causing symptoms of severe pelvic congestion and recurrent miscarriages (8 total) in a 41 year old female. The patient was treated with stenting of the compressed retroaortic portion of the IVC/left renal vein. Four months post-procedure, the stent remained patent and the patient reported considerable improvement in their venous congestion symptoms. Most notably, as of the writing of this report, the patient is 38 weeks pregnant. Conclusions: The case is notable for its severe symptomatology of pelvic venous disease including recurrent miscarriage. More importantly, it represents the first documented case of successful retroaortic endovascular management of such a venous anomaly, in which the entirety of the typical IVC drainage occurred via a compressed left-to-right retroaortic crossover.