First Lieutenant Woodruff was a crew member of a C-47A Skytrain transport with the 21st Troop Carrier Squadron, "Kyushu Gypsies", 403rd Troop Carrier Wing (Provisional). On 29 April 1952, his aircraft was participating in the evacuation of the American wounded in Korea. It was enroute from Seoul to Cho-do Island off the west coast of North Korea when it crashed into the sea near the beach at "Dentist C," killing all eight on board.

Woodruff was awarded the Purple Heart, the Korean Service Medal, the United Nations Service Medal, the National Defense Service Medal, the Korean Presidential Unit Citation and the Republic of Korea War Service Medal.