On 1 June 1945 Crew 30 on their 14 th mission took part in the Osaka strike. Just after landfall that day, Orr and his crew had trouble with an engine, but they refused to abandon the mission and went onto the target.

Just moments after bombs away, direct flak hit struck another engine and put it out of commission. Then shortly after land's end, the propeller broke from the engine that had first given them trouble and struck the B-29's fuselage with great force. A gaping hole was torn in the airplane, placing it imminent danger of breaking up in the air.

Working from the right side of the plane, Orr and his pilot, Lt. Monte Frosham, were able to bring the bomber under some measure of control and maintain flight through some five hundred miles of turbulent frontal weather on instruments in a right-wing-low, nose down altitude. The B-29 was in perilous condition with accumulated damage now mounting to the loss of two engines, a flak hit in the third, damage to the flight controls the whole plane would bend and the crew thought it would surely fall apart in mid-air.

After flying for several hours in this extremely dangerous state, the plane finally came out of the overcast and sighted a small-uninhabited island (Sofu Gan). It was then that Orr ordered the crew to bail out.

Then one of the bravest acts of the 39th Group's history took place. Edward Kanick, flight engineer couldn't swim, so Monte Frodsham took him on his back and jumped from the stricken plane. Monte hoped that he would be able to assist Kanick when they got into the water. But the force of the air tore Kanick from Monte's back and they fell separately.

Staff Sergeant James Schwoegler, Radio Operator, had stayed in the crippled plane until the last minute to assure himself that the ground station had received his position report of the bail out.

Orr remained with his plane and was the last to leave. Although he was barely managing to stay in flight with the one engine he had left, he refused to bail out until he was sure that all his men were out safely. He circled the spot where they had jumped until he saw all of them in the water, and then, despite the fact that the B-29 was rapidly loosing altitude and might blow up and any moment, he flew it away from the vicinity so that it could not possibly hit any of the survivors in the water when it crashed.

Then Bill Orr jumped at a dangerously low altitude. He got into the water safely and was later picked up with the rest of the other men, by Navy rescue submarine.

Lt. Orr was personally presented with the Distinuished Service Cross by General Spaatz.