Even though only one of the path-finding flights was completed in a single day, Praeger and Lipsner determined that the New York – Chicago flyway would open that fall. Through fits and starts and postponements, the service started up on December 18, 1918. If Praeger believed in signs, he might have called off the attempts after watching pilot Leon Smith return to Belmont Field shortly after he took off at 6:20 a.m. because of an overheated engine. Instead, pilot and mail were loaded into a second de Havilland and Smith took off for the second time. He got lost on his way to Bellefonte, Pennsylvania, landing at nearby State College to get his bearings. When Smith failed to show up at Bellefonte with the west-bound mail, the pilot stationed there, Edward A. Johnson, took off for Cleveland without it. Johnson, too, got lost, and was forced to land short of the Cleveland runway as darkness settled in.
Amazingly, the news from Chicago was even worse. A crowd of spectators and reporters arrived that morning for the historic east-bound flight. While there was mail and a pilot ready to go, there was no airplane. The aircraft that was to be used that morning had crashed on its way to Chicago the day before. After a few hours, the crowd wondered away. An airplane was finally located and sent on its way late that afternoon.
Praeger, unwilling to give up, kept the operation going. Two more pilots left New York City for Cleveland the next day. Neither made it there that day. Praeger sent two more pilots out of New York City the third day. Both returned to Belmont Field with engine trouble. Two days after the service had began, not a single airplane had reached Chicago with New York mail. The stubborn Praeger did not admit defeat until after four full days of failed flights. Confident even in defeat, Praeger announced that the service would be suspended for 10 days for reorganization.
The problems of this overly ambitious program could not be solved in 10 days, but that time gave Praeger's managers and pilots the time they needed to outline the worst problems of the system – poorly constructed engines, badly constructed airplanes, and pilots inexperienced with a route that would become known as one of the most difficult in the country. Quickly changing weather conditions over the Allegheny Mountains earned the area a pair of ominous nicknames from airmail pilots, "Hell's Stretch," and "Pilot's Graveyard."