Chronic refractory venous hypertension is a common complication following repeated central venous cannulation performed as a temporary vascular access for dialysis in patients with chronic renal failure. The symptoms of venous hypertension may diverge from being asymptomatic to severe edema, ulceration, headaches, bloating, and blackouts, especially if the patient has a surgical arteriovenous fistula for dialysis in any of his upper limbs. Treatment options for such patients are mainly directed toward endovascular management via balloon angioplasty and possibly stenting of the stenosed vein. Resistant lesions or cases with total venous occlusion coerce surgeons to consider surgical bypass. We present a case of a 43-year-old patient with history of renal impairment and repeated bilateral central venous cannulation for dialysis. The patient experienced superior vena cava syndrome with bilateral total occlusion of the internal jugular veins and both subclavian veins (with an occluded previously inserted stent) along with the superior vena cava. An extra-anatomical bypass was done from the left internal jugular vein to the left external iliac vein using a synthetic silver Dacron ringed graft. The procedure was successful and resulted in relief of the patient's symptoms and a dramatic improvement of the patient's quality of life. Superior vena cava syndrome represents 1 of the most challenging complications for patients with chronic renal impairment and repeated central venous cannulation. The endovascular approach is currently gaining popularity as the first line of treatment for such patients. However, surgical management is sometimes the only available option when the endovascular approach is not technically feasible. Our case, along with others, shows that an extra-anatomical synthetic graft bypass can be a reliable, less invasive option for the management of superior vena cava syndrome once surgical intervention is inevitable.