No. 460 Squadron participated in 1,000-bomber raids against Cologne, Essen and Bremen in May and June 1942. Brill was promoted to acting flight lieutenant in July, and completed his first tour of operations, numbering 31 sorties, on 11 August. He was seconded to the RAF as an instructor in November 1942, returning to No. 27 Operational Training Unit at Lichfield. He spent the next eleven months there, leading a training flight and gaining promotion to acting squadron leader in April 1943. In August, he was best man at the wedding of his friend and fellow RAAF pilot, Arthur Doubleday. The press would come to refer to the pair as the "Flying Twins", as their wartime careers closely paralleled one another—both men came from the Riverina district, joined the Air Force together on Remembrance Day 1940, arrived in England in August 1941, flew Wellingtons in No. 460 Squadron, volunteered for second tours in Bomber Command, and received many decorations and promotions in tandem. Doubleday would go on to survive the war and become active in civil aviation.