444 Squadron was first activated at Rivers, Manitoba on 1 September 1947.
Equipped with Chipmunks and Austers and designated 444 Air Observation Post Squadron (RCAF), it performed the duties of aerial artillery observations and ranging for the Royal Canadian Artillery (RCA). Although designated for the first time as 444 Squadron on 1 September 1947, it was in fact descendant from three other Canadian operational wartime squadrons: 664,665, and 666. On 1 April 1949, the squadron's duties were absorbed by the Light Aircraft School of the Canadian Joint Air Training Center (CJATC), and 444 Squadron was reformed as the RCAF's newest fighter squadron to be equipped with Mark IV Sabre aircraft. Although initially assigned to Canada's Air Defence Command and based at RCAF Station St Hubert, Quebec, 444 Squadron had already been identified as the twelfth and last Sabre unit to be formed, and was to complete the RCAF's existing NATO commitment in Europe. On 25 August 1953, 444 Squadron participated in Leap Frog IV, and on 4 September took up residence in Baden-Soellingen, West Germany where during the ensuing ten years the squadron was an active member of 4 Wing. Throughout this period 444 Squadron underwent several aircraft upgrades, progressing from the Mark IV to the Mark V and finally the Mark VI Sabre.
On 1 March 1963, 444 (Sabre) Squadron was deactivated in response to the decision to re-equip with the newly acquired Canadair CF-104 Starfighter. Two months later, on 27 May 1963, 444 (Strike/Attack) Squadron was reactivated at Baden-Soellingen. The squadron continued to operate in Europe in the role of strike/attack until 31 March 1967 when once again it was disbanded as a result of the decision to reduce the Air Division strength in Europe to six squadrons.
On 1 October 1972, 444 Squadron, after remaining dormant for five years, was again given active status when 444 Tactical Helicopter Squadron was formed as an integral unit of 4 Canadian Mechanized Brigade Group (4 CMBG) based in Lahr, and assigned the role of providing Tactical Aviation Support to 4CMB G. As was the case in 1947 the squadron found itself supporting the Army manned with personnel from "C" Squadron, the Royal Canadian Dragoons; The Air Observation Post (Air OP) troop of the 1st Regiment, Royal Canadian Horse Artillery; the Command and Liaison Flight of4CMBG HQ and Sigs Sqn and the Aircraft Platoon of 4 Service Battalion. In addition to the duties associated with these areas of responsibility, 444 Sqn also assumed the critically important task of coordinating all tactical aviation resources assigned to the 4CMBG area of responsibility, particularly the integration of attack helicopters of other allied armies.
As part of the closure plans for Canadian Forces Europe, 444 Squadron was disbanded on 1 April 1992. Since its start as a helicopter squadron in 1972 it has flown over 90,000 hours supporting countless exercises, and participating in humanitarian work throughout Europe.