In December 1940, Errol Barrow, along with 11 other of his countrymen who became known as "The Second Barbadian Contingent", enlisted in the Royal Air Force to serve during World War II. His sister Dame Nita Barrow recounted the event in her eulogy to him at his funeral. "I as the big sister packed his clothes ready for his move to the College. Then as he was about to leave a couple of days later, he calmly announced that he would not be going to College. 'I'm going to England. I've joined the Royal Air Force.' "After joining the RAF Volunteer Reserve in London as an Aircraftmen 2 (AC2), Barrow underwent initial training for light bomber crews at RAF Benson. He was then stationed at RAF Marham and trained as a wireless operator. By January 1942 he had been promoted to AC1 and thereafter undertook an eighteen-month navigator training course in Canada. Barrow was awarded his Air Navigator wings and promoted to Sergeant on 25 November 1943.