He traveled to England and joined the Royal Flying Corps in April 1916, being commissioned by the RFC in April. On 29 July 1916 he was posted to No. 8 Squadron RFC flying B.E.2Cs and Ds on observation duty. On 18 September 1916, flying a B.E.2D, he and his observer gained their first victory by downing a Roland CII. Caldwell as a natural, after scoring this first victory, he was reassigned to 60 Squadron in November 1916.
He received the Military Cross on 17 September.
Returning to England in October, he served as an instructor until March 1918 when he was promoted to Major and given command of 74 "Tiger" squadron equipped with the S.E.5a, which he took to France on 30 March.
Before the war was over, Caldwell survived a mid-air collision and scored sixteen more victories bringing his total to 25. Virtually all of his victims were single-seat fighter/scouts. But for his poor marksmanship, some thought that Caldwell might have been one of the highest scoring aces of the war.
He was awarded the Distinguished Flying Cross in December 1918.
The citation being "A fine fighting airman of courage and determination. On 4th September, when on offensive patrol, he, in company with another machine, attacked four Fokker biplanes; one of these was driven down by this officer. He has accounted for five enemy machines."
Caldwell would also receive the Croix de Guerre from the Belgians.
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