May-Thurner syndrome (MTS) is a clinical condition characterized by the compression of the left iliac vein by the right iliac artery. This condition predisposes the patient to deep venous thrombosis (DVT). We present the case of a 30-year﻿-old female who arrived at the emergency department of our facility with progressive left leg swelling for four weeks, with low-risk probability for DVT. Examination revealed left leg swelling with pitting edema extending up to the knee. Her calf muscle was tender to palpation. Dorsalis pedis, anterior tibial, and posterior tibial pulsations were fairly palpable due to the edema; however, the rest of her pulsations were appropriately felt. Therefore, the provisional diagnosis of possible DVT was made, and further investigations were requested. We present this case intending to highlight the clinical presentation of May-Thurner syndrome, its diagnosis, and treatment.