The 50th Education Squadron (50 ES) was first organized as the 50th Aero Squadron on 6 August 1917 at Kelly Field #1, Texas. The unit flew observation missions in the American built DH-4 over the battlefields of World War I. While in Europe, this unit saw combat at St. Michael, Lorraine, Meuse Argonne, and other locations as part of I Army Corps. The squadron adopted the famous Dutch Girl insignia, trademark of Old Dutch Cleanser. To the flyers of the 50th Aero Squadron, the Dutch Girl meant one thing: "Clean up on Germany." The insignia was painted on the aircraft, and squadron members wore matching pins above the right breast pocket on their uniforms. On 6 October 1918, 1Lt Harold E. Goettler and 2Lt Erwin R. Bleckley, of the 50th Aero Squadron were shot down near Bienville, France, while attempting to drop supplies to a battalion of the 77th Division, surrounded by the enemy in the Argonne Forest. Both died from their wounds and were posthumously awarded the Congressional Medal of Honor during World War I.

In 1938, the unit was redesignated the 50th Reconnaissance Squadron and moved to Hickam Field Hawaii where they flew B-18s. On 22 April 1942, the 50th became the 431st Bombardment Squadron and entered combat in the Pacific. The squadron flew a variety of aircraft including the B-24, F-13, F-7, C-46, C-47, FB-17, and T-43A. They participated in numerous campaigns in the Far East to include Air-Offensive-Japan, Guadalcanal, and the China Offensive. The unit earned the Distinguished Unit Citation and the Presidential Unit Citation for its services in the Pacific. The unit was subsequently deactivated on 20 October 1947.

The squadron was reactivated at the United States Air Force Academy on 1 October 1983 and designated the 50th Airmanship Training Squadron. In 1994, the unit earned its fourth Air Force Outstanding Unit Award, three of them consecutively, in its time at the Academy. In November 1994 the squadron was redesignated as the 50th Training Squadron. The summer of 1997 saw the last flight of the T-43A for the squadron with a change in direction for the squadron mission and a loss of funding for the Buckley ANG Base unit which supported T-43 operations. In January 2001 the squadron was redesignated the 50th Education Squadron, reflecting the squadron's change in mission.

The silhouette of a DH-4 on the squadron patch proudly displays the unit's link to a colorful heritage. The Flying Bobcat, also on the patch, represents the 200th Airlift Squadron (200 AS), Colorado Air National Guard. The Guard unit flew and maintained the T-43A, the last aircraft used by the 50th. Today, the focus of the 50th mission is in the classroom, supporting the instruction of US Air Force Academy Cadets in Military Strategic Studies.