Beyond May-Thurner: When CTA Uncovers a Triple Venous Compression

May-Thurner Syndrome (MTS) is an anatomical condition characterized by the compression of the left common iliac vein by the right common iliac artery, often leading to venous thrombosis. It is underdiagnosed, with most cases presenting in females between 20–40 years. We present the case of a 68-year-old female with Sharp syndrome, a known connective tissue disease, who presented with unilateral lower limb discomfort. Imaging via computed tomography angiography (CTA) revealed compression of the left common iliac vein, alongside Nutcracker Syndrome and pelvic venous congestion. Given the absence of thrombosis and stable symptoms, the patient was treated conservatively with analgesics and venotonic agents. This case highlights the importance of CTA in diagnosing MTS and related syndromes, especially in complex cases with overlapping vascular anomalies.