Following Roi Namur, Webster was appointed Intelligence officer of 1st Battalion and took part in the Battle of Saipan in June 1944. He was wounded by enemy fire on June 15 and evacuated to the rear for treatment. Webster was declared fit for duty soon afterwards and joined 2nd Battalion, 24th Marines as major and executive officer under the command of Major Frank E. Garretson. He took part with that unit in the capture of Tinian in August of that year and was awarded the Bronze Star Medal with Combat "V" for his service at Saipan and Tinian and Purple Heart for wounds sustained at Saipan.