He attended the School of Military Aeronautics at Princeton University from March to June 1918 and was then assigned to Chanute Field, Illinois.

[1] Webster entered the Air Corps Tactical School (ACTS) at Maxwell Field, Alabama, in August 1933.

[2] For the next three years, Webster worked with other ACTS instructors—Harold L. George, Donald Wilson, Muir S. Fairchild, Haywood S. Hansell and Laurence S. Kuter—to determine how best to use precision bombing techniques that were under development to destroy small, vital enemy targets during the opening phase of a war, so as to hinder the enemy's potential to wage a lengthy war.

In the Air Force we have the only agency with direct access to the fundamental objectives in war ... with a spirit that is immunized from the effects of army doctrine by a growing consciousness of its own independent power in war ... A casual survey of the evidence now available, must be convincing, that the creation of a separate and independent Air Force is the rational, simple, and inevitable solution to the problem.

[3]Webster further asserted to the commission that "Ground officers were not aware of the fact that a properly organized attack, once launched in the air, cannot be stopped.

[1] United States became directly involved in World War II in December 1941 while Webster was stationed in Washington.

Webster continued to work there to organize the massive training programs undertaken by the United States Army Air Forces (USAAF).

Remaining in the nation's capital, in March 1942 Webster joined the Operations Division of the War Department General Staff.

In this role, Webster presented the Amelia Earhart Scholarship to Virginia L. Sweet, a WASP aviator, in late 1949.

[10] In June 1950, Webster was appointed chief of the Air Section, Joint Brazil-U.S. Military Commission, at Rio de Janeiro, Brazil.

[1] Moving to USAF Headquarters, Washington, D.C., on January 22, 1953, Webster was designated Air Force and Steering and Coordinating Member for Military Representation, U.S.