May-Thurner Syndrome, left iliac vein compression by the right iliac artery, is a congenital permissive lesion that requires an additional insult prior to the onset of symptoms. We present a case of a 31-year-old gravida 1 para 0 at 28.6 weeks who presented to the emergency room with a 2-month history of progressive lower left leg swelling since 21.2 weeks’ gestation. The patient endorsed incidence of domestic violence at 17 weeks’ gestation. The patient had a twin sister who was also pregnant and had not experienced these symptoms. Physical exam revealed 3+ pitting edema in the left lower extremity from ankle to groin. There was left calf tenderness with negative Homan’s sign bilaterally. Overall finding on magnetic resonance angiography revealed severe compression of the upper left common iliac vein and lower inferior vena cava by gravid uterus. Conservative management and anticoagulation is instrumental in preventing veno-thromboembolic events in pregnancies complicated by MTS.