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Dehart remained at San Jose until the start of World War I in 1917 when he enlisted with the Government and served as a civilian flight instructor for a time at Rockwell Field, North Island, San Diego, California. There he started as a Junior Instructor and later was promoted to Senior grade. He remained at Rockwell Field until about mid-1918 when the Government had an ample supply of pilots and was no longer interested in civilian instructors. In leaving he left an enviable record of having logged 650 hours of instruction time without an accident.
He then joined Otto Timm, another Rockwell Field instructor who had also left, and started to build a new training plane which he hoped would replace the Curtiss [[?]]. This project was short-lived, however, and soon folded up.
About this time DeHart received a letter from Max Miller, also a former Rockwell Field instructor, saying that he had joined the newly established Air Mail Service and that they were looking for pilots who had a substantial amount of flying time. As a result DeHart went to Washington, enlisted in this Service and on August 19, 1918 became one of the first five civilian pilots in the Air Mail Service. He was selected for the route from Washington D.C. to New York City and was one of the first pilots to fly the full distance with one stop a Philadelphia. The total flying time for his first run was 2 hours, 48 minutes.
Up until that time one pilot would fly from Washington to Philadelphia, the another would take over and fly into New York. On September 18th he flew from New York to Washington in weather so bad he had to wait for over an hour before starting, to find a spot clear enough to even take off at Belmont Park.
On October 16th DeHart made a very renowned historic trip when he carried Douglas Fairbanks, Sr. as authorized mil on his Washington to New York run, as a publicity stunt by the Post Office Department, to publicise the 4th Federal Liberty Loan Drive. After being photographed and interviewed by the press the authorities stuck an air mall stamp on Fairbanks' forehead and loaded him into the plane's mail compartment on top of the mail bags, and although it must have been very uncomfortable, he did not complain and made the trip in stride. The
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