On Saturday, October 27, Anderson took off on his sixth mission over Cuba in a U-2F Dragon Lady (AF Serial Number 56-6676, former CIA Article 343), from a forward operating location at McCoy Air Force Base in Orlando, Florida.

[5] A few hours into his mission, he was shot down over Banes, Cuba by one of two Soviet-supplied S-75 Dvina (NATO designation SA-2 Guideline) surface-to-air missiles that were fired at his aircraft by the orders of two Soviet generals, stationed in Havana.

[6][7] This would mean Anderson was killed when fragmentation from the exploding proximity warhead punctured his pressure suit, causing it to decompress at high altitude.

On October 31, Acting United Nations Secretary-General U Thant returned from a visit with Premier Fidel Castro and announced that Anderson was dead.

[12] Seven more airmen died when a Boeing C-135B Stratolifter delivering ammunition to Naval Base Guantanamo Bay in Cuba stalled and crashed on approach on October 23.

During this period of great national crisis, Major Anderson, flying an unescorted, unarmed aircraft, lost his life while participating in one of several aerial reconnaissance missions over Cuba.

While executing these aerial missions, Major Anderson made photographs which provided the United States government with conclusive evidence of the introduction of long-range offensive missiles into Cuba and which materially assisted our leaders in charting the nation's military and diplomatic course.

Through his extraordinary heroism, superb airmanship, and aggressiveness in the face of the enemy, Major Anderson reflected the highest credit upon himself and the United States Air Force.