Nutcracker syndrome, also called renal entrapment syndrome, is a rare clinical entity in which the left renal vein is obstructed between the aorta and superior mesenteric artery. As the renal vein drains via collaterals, engorgement of the pelvic vasculature can lead to pelvic congestion syndrome. This has been associated with severe pain and can require nephrectomy when associated with a renal origin. We present the case of a patient in her early 30s with one native left kidney and nutcracker syndrome leading to disabling pain. After several months of evaluation she was diagnosed with pelvic congestion syndrome. Treatment alternatives were considered and she underwent left renal autotransplant into the right iliac fossa. The left nephrectomy was performed laparoscopically with hand assist, and the transplant completed intraabdominally via the nephrectomy incision. Postoperatively her pain improved and she has returned to work and a normal life.