The 492^nd FS was originally constituted as the 55th Bombardment Squadron, was activated in January 1941 and redesignated as the 492^nd Fighter-Bomber Squadron in August 1943. The squadron flew B-18, A-20, P-35, P-39, P-40, and P-47 aircraft during World War II and served with distinction.

After deactivation in November 1945, the squadron was reactivated at Chaumont AB, France in July 1952, During this time, the squadron received F-84G’s (Jul 52 - Feb 54), F-86F’s (Nov 53- Nov 56), and F-100D’s (Sep 56 - Apr 72), before transferring to RAF Lakenheath in 1960. The squadron later transitioned to F-4D's in October 1971, to F-111F's in March 1977 and to the F-15E in May 1992. Throughout its proud heritage and service, the 492^nd has significantly contributed to NATO and the United States Air Forces in Europe (USAFE). In recognition of these contributions, the 492^nd was named the Outstanding Fighter Squadron in USAFE for 1986.

Executing combat missions from RAF Lakenheath, the 492^nd Fighter Squadron set the standard for "Anywhere, Anytime". Between March and June of 1999, 492^nd FS aircrews and maintainers employed the world's premier multi-role fighter, the F-15E Strike Eagle. The Madhatters flew 475 successful Combat missions, deployed 400 tons of bombs in an unprecedented fashion - from the deployed locale at Aviano, AB Italy, as well as from the United Kingdom. The 492^nd played a pivotal role in stopping the Serb offensive in Kosovo, and setting the foundation for the NATO-led international peacekeeping force into Kosovo.

Nicknamed the "Madhatters", the squadron is known for its tradition of adopting the headgear unique to the country in which the squadron is based. Accordingly, the aircrews wore berets in France, and now in the United Kingdom, squadron aircrews wear both the Scottish Glengarry, for informal occasions, and the traditional British Bowler for formal events. The squadron emblem is also noteworthy as it depicts the versatility of this combat-proven unit. A fierce red Kestrel, a Falcon known for its tremendous flying ability, dominates the emblem. Below the Kestrel is the torch of freedom. Highlighting the 492^nd's premier role in the Statue of Liberty Wing.