Established as a Boeing B-17 Flying Fortress heavy bombardment squadron in early 1942; trained under Second Air Force. Flew antisubmarine patrols off the California coast from, late May–early June 1942, then over the Mid-Atlantic coast during June–July 1942. Deployed to European Theater of Operations in August 1942, being assigned to VIII Bomber Command, one of the first B-17 heavy bomb squadrons assigned to England. Engaged in strategic bombardment operations over Occupied Europe attacking enemy military and industrial targets. Reassigned to Mediterranean Theater of Operations as part of Operation Torch invasion of North Africa. Operated from desert airfields in Algeria and Tunisia during North African and Tunisian campaign. Assigned to Northwest African Strategic Air Force during Invasion of Sicily and later Italy in 1943. Allocated to Fifteenth Air Force for strategic bombing of Nazi Germany and occupied Europe. Attacked enemy targets primarily in the Balkans; Southern France; Southern Germany and Austria from southern Italy; engaged in shuttle bombing missions to airfields in the Soviet Union during the summer of 1944. Personnel largely demobilized after German capitulation in May 1945; squadron reassigned to the United States and was programmed for conversion to B-29 Superfortess operations and deployment to Pacific Theater, plans canceled after Japanese capitulation in August 1945. Aircraft sent to storage and unit inactivated largely as a paper unit in October 1945.
From 1958, the Boeing B-47 Stratojet wings of Strategic Air Command began to assume an alert posture at their home bases, reducing the amount of time spent on alert at overseas bases. The SAC alert cycle divided itself into four parts: planning, flying, alert and rest to meet General Thomas S. Power's initial goal of maintaining one third of SAC’s planes on fifteen minute ground alert, fully fueled and ready for combat to reduce vulnerability to a Soviet missile strike. To implement this new system B-47 wings reorganized from three to four squadrons. The 419th was activated at Lockbourne Air Force Base as the fourth squadron of the 301st Bombardment Wing. The alert commitment was increased to half the squadron's aircraft in 1962 and the four squadron pattern no longer met the alert cycle commitment, so the squadron was inactivated on 1 January 1962.
Flight Test Squadron
Reactivated as a flight test squadron at Edwards AFB in 1989 taking over the Air Force Flight Test Center Strategic Systems Division. Also operated UAV test program 1994–2000 when the UAV program was realigned. Gained B-1 Lancer program from the 410th Flight Test Squadron in 1991 when the 410th was moved to Palmdale and took over the F-117 Program. Gained B-2 Spirit program from the inactivating 420th Flight Test Squadron on 30 December 1997.
Lineage
; 419th Bombardment Squadron
Constituted as the 29th Reconnaissance Squadron on 28 January 1942
Redesignated 419th Bombardment Squadron, Medium on 20 August 1958
Consolidated with the 6519th Test Squadron as the 6519th Test Squadronon 1 October 1992
; 419th Flight Test Squadron
Designated as the 6519th Test Squadron and activated, on 10 March 1989
Consolidated with the 419th Bombardment Squadron on 1 October 1992