Nutcracker syndrome is a rare disorder characterized by extrinsic compression of left renal vein by the superior mesenteric artery and aorta. Prevalence of the disease is unknown, but presents most commonly with gross hematuria and flank pain. Diagnosis requires a high index of suspicion and treatment consists of a wide range of vascular surgical options with a more recent focus using an endovascular approach. We present a case of a 29-year-old female with continuous gross hematuria and flank pain from a segmental artery pseudoaneursym secondary to nutcracker and pelvic congestion syndrome.