American International Airways Flight 808 was a cargo flight operated by American International Airways (now Kalitta Air) that crashed on August 18, 1993 while attempting to land at Leeward Point Field at the Guantánamo Bay Naval Base in Cuba.

This was canceled after N808CK suffered mechanical problems, so the accident crew were rescheduled to fly to Chambers Field in Norfolk, Virginia to pick up and deliver the freight bound for Guantánamo Bay and return to Atlanta.

It was transporting mail and perishable food to the Guántanamo Bay Naval Base as per AIA's contract with the US Navy.

The nose pitched down as the wings rolled toward 90 degrees and at 16:56, the aircraft struck level terrain 1,400 feet (470 yd; 430 m) from the end of the runway.

The cockpit had separated on impact from the main wreckage and tumbled across the ground, coming to rest inverted with all 3 crew members alive inside, albeit with serious injuries.

Special permission was granted for a medical aircraft to overfly Cuban airspace to save time transporting the crew to hospital.

During the approach to Runway 10, the air traffic controller told the crew to remain within the airspace designated by a strobe light mounted on the Cuban border fence.

This aggravated the effects of fatigue on the crew, with Captain Chapo, in particular, observed suffering from various symptoms, including impaired judgment with his decision to land on Runway 10, his cognitive fixation on trying to locate the strobe light, the poor communication with his crew about their decreasing airspeed and his slow reaction time in avoiding and recovering from the stall.

[2][4] The investigation into the accident also revealed that the crew, already fatigued from a large amount of sleep debt and an extensive shift, did not have to accept the additional flights to Norfolk, Virginia and Guantanamo Bay, but did anyway for fear of losing their jobs.

The NTSB determined the probable causes to be: "The impaired judgement, decision-making and flying abilities of the captain and flight crew due to the effects of fatigue; the captain's failure to properly assess the conditions for landing and maintaining vigilant situational awareness of the airplane while manoeuvring onto final approach; his failure to prevent the loss of airspeed and avoid a stall while in the steep bank turn; and his failure to execute immediate action to recover from a stall.

[4] The NTSB issued a recommendation to the Federal Aviation Administration to review and update regulations on crew scheduling and duty time limits to incorporate the latest research into the effects of fatigue.