 While in training he was promoted to lieutenant on June 7, 1925, and was designated a naval aviator on September 11, 1925, becoming an aviator qualified in both fighters and flying boats.On November 2, 1936 Lieutenant Commander Cunningham reported for duty involving flying as Commanding Officer of Fighting FIVE (VF-5).The squadron would become part of the USS Yorktown (CV-5) Air Group flying the Grumman F2F-1.