Calabria returned to military duty shortly before Italy's entry into World War I, and was assigned to the Battaglione Aviatori in December 1914. After pilot's training he was posted to the 4a Squadriglia Artiglia, an artillery coordination unit and then to 2a Squadriglia in January 1916. In May of that year Calabria underwent further training on Nieuports and he was assigned to 1a Squadriglia as a fighter pilot. He won his first victory there, shared with Francesco Baracca in August 1916. He would end the year in the 70a Squadriglia with 2 confirmed and 2 unconfirmed victories.
After recovery, he was handed command of 10th Gruppo. In late October 1918, he was shot down while flying over the Austrian lines but managed to land in friendly territory.
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