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Shipments fell 37 percent year-over-year, the Chicago-based manufacturer said on Tuesday, to 239 commercial planes.
The decline is poised to allow rival Airbus to take over as the world's largest planemaker. The Netherlands-based company delivered 389 aircraft in the first half of 2019, a 28 percent increase year-over-year.
Boeing has suffered since the international grounding in March of its Max jet, an update to the popular 737 narrow-body aircraft. Federal officials previously estimated that the fleet could be out of service until the end of 2019.
On Sunday, Saudia Arabian budget airline flyadeal said it would forgo an order for 50 Boeing Max jets, instead opting for rival Airbus A320neo. But in a vote of confidence, British Airways parent-company International Consolidated Airlines Group SA in June said it would order 200 Max planes.
Boeing previously cut production of the Max jet to 42 planes per month and experts say another decrease could be looming. The bulk of the payment for new aircraft tends to come once the plane is shipped to customers, increasing pressure on the company to return the Max to flight.
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Boeing is working with the Federal Aviation Administration and global regulators to gain clearance for a software update intended to fix the issues that led to the Ethiopian Airlines and Lion Air crashes.
In the meantime, carriers like American Airlines and Southwest Airlines have extended the potential for cancellations through Labor Day as a result of the grounding.
CEO Dennis Muilenburg has also been on a global apology tour to try to assuage concerns from the flying public over the safety of Boeing's signature aircraft.
The company is directing $100 million to help the families and communities impacted by the crashes.