This study reviews the operative technique of external jugular vein to the internal jugular vein (IJV) bypass and discusses its advantages of decreasing postoperative complications in bilateral neck dissection patients. A retrospective chart review was performed on 2 patients at a single institution with prior bilateral neck dissection and jugular vein bypass. The tumor resection, reconstruction, bypass, and postoperative management were led by the listed senior author (S.P.K). An 80-year-old (case 1) and a 69-year-old (case 2) underwent bilateral neck dissection with the creation of a micro-venous anastomosis. This bypass allowed for improved venous drainage without adding significant time or difficulty to the procedure. Both patients recovered well in the initial postoperative period with maintained venous drainage. This study describes an additional technique that the trained microsurgeon can consider during the index procedure and reconstruction that can benefit the patient without adding significant time or technical challenges to the remaining portion of the procedure.