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Nutcracker Syndrome is a rare condition secondary to either compression of the left renal vein in its normal anatomic position by the superior mesenteric artery and aorta, or rarely, when the left renal vein is in a retroaortic position, compressed between the aorta and the spine. Left renal vein compression varies widely in presentation and severity, ranging from asymptomatic imaging findings, to chronic pelvic or flank pain. While left renal vein transposition remains the most common management modality, there is growing acceptance for other surgical interventions as well as endovascular treatments–particularly stenting. However, there remains a scarcity of evidence for these less invasive techniques. We conduct a review of the recent literature and discuss the diagnosis and current management strategies for nutcracker syndrome. We also revisit a unique case of nutcracker syndrome in a female patient with a history of chronic pelvic pain and venous congestion wherein transposition of the left renal vein resulted in complete resolution of her symptoms.