May-Thurner syndrome (MTS) is a known structural risk factor for deep vein thrombosis (DVT) and embolism. In patients with a patent foramen ovale (PFO), emboli originating from the deep veins are able to paradoxically reach the systemic circulation via the PFO, consequently resulting in transient ischemic attacks (TIA) or stroke.We report the case of a 31-year-old pregnant woman, with a recent history of TIA, who presented with chronic bilateral numbness, pain, and swelling in the lower extremities. On imaging, she was found to have a PFO and MTS. Her pregnancy was subsequently terminated. This decision was made independently by the patient. Her care team did not advise her to terminate her pregnancy as there was no specific medical reason to do so. However, the patient was in significant physical pain and distress and ultimately was not comfortable continuing with the pregnancy. This highlights the complex, multifactorial decision-making process that pregnant patients with comorbid health conditions undertake. The patient then underwent transcatheter PFO closure and stents were placed bilaterally in the left and right common iliac veins. Following the stent procedure, lower extremity symptoms swiftly resolved, allowing the patient to significantly improve her ability to ambulate. There have been no signs of TIA since her procedures, and her venous symptoms have been stable.In patients with TIA or stroke from a paradoxical embolism, MTS should be considered as a potential etiology. Endovascular intervention to treat the underlying MTS should also be considered to decrease the risk of recurrent DVT and embolism.