Deep vein thrombosis (DVT) is a common medical condition, but the predisposing anatomical factors, which may be amenable to definitive treatment, are usually overlooked. Therefore, a high index of clinical suspicion is the key to early diagnosis. We report here one such case of May-Thurner syndrome (MTS) to raise awareness. MTS (also known as iliac vein compression syndrome) should be suspected in cases of extensive DVT of the leg, particularly involving the iliac vein on the left side. The prognosis is improved with thrombolysis followed by angioplasty and stent to address the venous stenosis.