Nutcracker syndrome is a clinical entity leading to renal venous hypertension due to extrinsic compression of the left renal vein by the superior mesenteric artery. Current surgical therapy involves placement of an oversized renal vein stent with partial protrusion into the inferior vena cava (IVC) to relieve stenosis and prevent stent migration. Here, we present a patient with intractable pain and hematuria secondary to nutcracker syndrome who underwent left renal vein stent placement and developed recurrent symptoms due to flow-limiting kinking at the left renal hilum, with partial obstruction of the IVC from pseudointimal hyperplasia. This was treated with stent excision and construction of a left neorenal vein bypass. Thus, given these complications, we should perhaps revisit the recommendations for oversizing of the stent.