Despite occasionally debilitating health problems, Roosevelt served with the 2nd Raiders at Midway in early June 1942 and in the Makin Island raid on August 17–18, 1942, where he and 22 others were awarded the Navy Cross. In October, he was given command of the new 4th Raiders, but during training for an upcoming combat operation he became ill enough to be hospitalized by February 1943. Beginning in August 1943, he served in various staff positions for the duration of the war. He was attached to and landed with the U.S. Army's 165th Regimental Combat Team, 27th infantry Division during the invasion of Makin on November 20–23 and was awarded the Silver Star by the army. He was promoted to colonel on April 13, 1944. He was released from active duty in August 1945 and was placed on the inactive list in October 1945. That same month he became a Compatriot of the Empire State Society of the Sons of the American Revolution.