In July 1928 he entered the United States Military Academy in West Point, New York and on June 10, 1932,[2] he was commissioned a second lieutenant in the infantry.

In November 1933, Hobson received his pilot wings after graduating from primary and advanced flying schools at Randolph and Kelly fields, Texas.

After a year of being hospitalized, Hobson was assigned to the 22nd Bombardment Squadron in April 1940, and served at Hamilton Field, California, and Fort Douglas, Utah.

Three B-17s led by Hobson (then a major) completed the first flight from Hawaii to Australia over an emergency-devised South Pacific air route, arriving January 12, 1942.

Then he flew his B-17 Flying Fortress to Java in the Dutch East Indies, where his squadron had been diverted in an attempt to stem the Japanese advance.

In February 1952, Kenneth was named deputy director of manpower and organization at U.S. Air Force headquarters, Washington, D.C.