Airman Second Class Osborne was a crew member of a B-29A Superfortress Bomber with the 371st Bomber Squadron, 307th Bomber Wing. On 23 October 1951, the aircraft was shot down by enemy MiGs over Namsi Airfield, North Korea. He was taken Prisoner of War and was presumed dead on 28 February 1954. His remains were not recovered. His name is inscribed on the Courts of the Missing at the Honolulu Memorial.

Osborne was awarded the Air Medal, the Purple Heart with Oak Leaf Cluster, the Prisoner of War Medal, 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.