In July 1940, Woodruff assumed command of the 2nd Battalion,
23rd Infantry, the same outfit he had served with in World War I. After being promoted to the temporary rank of colonel on June 26, 1941, he then commanded the regiment, then stationed at
Fort Sam Houston,
Texas. On January 15 1942, over a month after the
Japanese attack on Pearl Harbor and the subsequent
German declaration of war against the United States, which brought the country into
World War II, he was promoted to the temporary rank of
brigadier general. Woodruff then became the assistant division commander (ADC) of the
77th Infantry Division, a unit of the
Organized Reserves, which was reactivated on March 25, 1942, and composed almost entirely of
conscripts (or "draftees"). On June 22, 1942, he was promoted again, this time to the temporary rank of
major general, shortly after he took over command of the division on June 5, during its pre-deployment training in
Fort Jackson,
South Carolina. He was awarded the
Bronze Star Medal. On May 22, 1943, Woodruff relinquished command of the 77th Division to Major General
Andrew D. Bruce, who was later to lead it in action where it served with distinction, and took command of the
VII Corps, then stationed in
England. This brought him into contact with two of his former West Point classmates.
Dwight D. Eisenhower, now a
four-star general and the
Supreme Allied Commander in Europe, was the first, and had been appointed to his new role in December 1943. The second classmate,
Lieutenant General Omar Bradley, was designated in October 1943 to command the
First Army for the upcoming
Allied invasion of Normandy, with Woodruff as one of his three corps commanders, along with Major General
Leonard T. Gerow, commanding the
V Corps, and Major General
Willis D. Crittenberger, commanding the
XIX Corps. All three men were well known to Eisenhower and Bradley, both of whom had seen service in the
Mediterranean Theater of Operations (MTO), but they were concerned about having three such senior commanders who all lacked experience in
amphibious operations or recent experience of battle in this war. Gerow, who was very close friends with Eisenhower and a protégé of General
George C. Marshall, the
Chief of Staff of the United States Army, managed to retain his position, but Crittenberger and Woodruff were relieved and replaced by two experienced division commanders, Major Generals
Charles H. Corlett and
J. Lawton Collins respectively. Woodruff was shuffled off to command of XIX Corps, Crittenberger's former command, for several weeks, before returning to the United States, and he handed over command to Corlett. He was awarded the
Army Distinguished Service Medal. Upon his return to the United States, Woodruff was deemed to be, in the opinion of Lieutenant General
Lesley J. McNair, the commander of
Army Ground Forces, "tainted goods and as such was ineligible for another corps". As a result, he assumed command of the
84th Infantry Division, then in training at
Camp Claiborne,
Louisiana, from March to June 1944. Like the 77th Division two years earlier the 84th was composed largely of draftees. Woodruff's chance at large-scale combat command finally came when he was sent to the
Southwest Pacific Area to command Army Garrison Force 248 on
Leyte. In November, the commander of the
Sixth Army, Lieutenant General
Walter Krueger, abruptly gave him command of the
24th Infantry Division in the place of the fired Major General
Frederick A. Irving. His welcoming reception in the
theater was celebrated at the
paratroop headquarters, fueled with five gallons of
torpedo alcohol, furnished by
United States Navy patrol boat sailors, as the key ingredient for liquid refreshments. Ironically, Woodruff proved adept at amphibious operations, making a series of twenty-five landings on
Mindoro in January and February 1945. He led his command in the five month
Battle of Mindanao to liberate that island from Japanese occupation. During the campaign he broke several ribs when he fell into a Japanese
spider hole. Although in great pain and unable to sleep for two weeks, he concealed the injury for fear of being declared unfit and sent home again. He was awarded an oak leaf cluster to his Army DSM, which he had earned earlier in the war, the
Silver Star with two oak leaf clusters, the
Purple Heart and the
Air Medal with an oak leaf cluster. ==Postwar==