The unit was first activated in 1942, flying Curtiss Kittyhawks as No. 14 (Fighter) Squadron with the RCAF Western Air Command due to the threat to Canada’s West Coast after the Pearl Harbor attack. The squadron moved to Alaska and participated on strafing and bombing missions against then-Japanese held Kiska during the Aleutian Islands Campaign.
The squadron was then renumbered the 442 Fighter Squadron and transferred to England in January 1944 where it flew attack and long-range bomber escort sorties in Northwest Europe. In 1945, the squadron was disbanded in England following the end of the WWII hostilities and reformed a year later at RCAF Station Sea Island on Sea Island in Richmond, British Columbia, in Canada, as an auxiliary fighter squadron with De Havilland Vampires. It was again disbanded in 1964.
In an article titled "442 Squadron, Sea Island Part-time Pilots" in the Fall 2001 edition of the Richmond Archives News, the writer says that in 1951, Canada went through a year of "protective re-armament" in response to the Cold War of the post WWII era. Part of the strategy was the expansion of RCAF Reserve Forces across the country in selected bases such as Sea Island. Men from around the Lower Mainland who came from a variety of jobs like Ernest Chan, gave up a few hours each weekend to break in on Vampire Jet fighters.
It was reformed during the 1968 unification of the Canadian Forces as 442 Communications and Rescue Squadron at CFB Comox before being redesignated to its current name of 442 Transport and Rescue Squadron and role, a few months later.