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Internal jugular phlebectasia (IJP) is a rare disease in which there is a fusiform dilatation of internal jugular vein, usually presenting as a neck mass in children. Accurate diagnosis from careful history, physical examination, and radiological study can be made. This case report intends to stress the importance of keeping IJP as differential diagnosis while dealing with such a swelling to avoid invasive investigations and inappropriate treatment. Internal jugular phlebectasia (IJP) is a congenital fusiform dilatation of the internal jugular vein that appears as a soft, compressible mass in the neck during straining or is triggered by the Valsalva maneuver. The possible differential diagnosis for the swelling could include a laryngocele, branchial cyst, cystic hygroma, cavernous hemangioma, and superior mediastinal cysts. This can affect any neck vein, especially internal jugular, external jugular, anterior jugular, superficial communicus in decreasing order. Color Doppler imaging confirms the diagnosis and is the gold standard, also CT venography was done. Our approach offers another surgical option to the treatment of the jugular vein phlebectasia with excellent results as it cures the patient of the swelling and at the same time does not hamper the venous drainage of the brain.