His tour of training with the Air Corps began with basic training in Amarillo, Texas. After basic training Woodland was sent to Las Vegas for gunnery school. When it came time to form together as a crew, Woodland became the ball turret operator for crew #35, 569th squadron. The crew conducted their phase training in Sioux City, Iowa. After the completion of their training, the crew were given a B-17 to transport to England. After they arrived, and handed off the B-17, the crew were transported to Framlingham to join the 390th. Woodland's first mission was on November 29, 1944. Within a month he would fly and complete 6 combat missions. But during his 7th mission to Hamburg, Germany on December 31, 1944, his plane would be shot down, forcing he and his crew to bail out. By the first day of the new year, Woodland would be taken as a prisoner of war by German forces. Woodland would be a captive until the end of the war in Europe, when he was liberated by American forces lead by General Patton. During his interview, Woodland recalls his time spent as a prisoner of war, and other experiences from his time in service.

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