Popliteal entrapment syndrome is an uncommon cause of intermittent claudication in young patients lacking atherosclerotic risk factors. ZS is a 16-year-old cisgender female with type 1 diabetes complicated by microalbuminuria, obesity (body mass index (BMI) = 45.86 kg/m²), and a history of perinatal stroke with residual right-sided hemiparesis, who presented with six months of worsening bilateral, exertional lower extremity pain. Common causes of chronic bilateral lower extremity pain include peripheral vascular disease and diabetic neuropathy. Less common etiologies include trauma, infection, or juvenile idiopathic arthritis. Given her risk factors, the patient's pain was initially managed as a diabetic neuropathy with pregabalin. Symptoms failed to improve, and she re-presented with positional coolness of the right lower extremity, diminished pulses of the bilateral lower extremities, and weakness in her toes. CT angiography demonstrated occlusion of the right distal superficial femoral and popliteal arteries and diffused tibial disease. Ultimately, the patient was discovered to have right-sided femoral-popliteal occlusion, and she required urgent femoral-tibial bypass. Despite an initial improvement in symptoms postoperatively, she continued to have lower extremity pain and recurrent arterial thrombi, even with antiplatelet and anticoagulation therapy. Eventually, the patient required a right-sided below the knee amputation. This case highlights the high index of suspicion that clinicians must have in young patients with lower extremity pain, both with and without atherosclerotic risk factors, as early intervention facilitates better outcomes. Introduction.