Amazon has lost two executives critical to the company’s drone-delivery operations, in the latest setback for an ambitious initiative that required significant investment but did not bring much success.

According to his LinkedIn profile, Prime Air lead pilot Jim Mullin left Amazon last month. According to a LinkedIn post, Robert Dreher, who reported to Mullin and was responsible for all Prime Air test operations, left last week for a position at Opener, which makes electric vertical take-off and landing aircraft.

Both employees worked at Prime Air headquarters in Pendleton, Oregon. Their departure was not widely publicized outside of their blogs, and neither responded to requests for comment via LinkedIn.

Amazon declined to comment on their departure.

The departures come at a critical time for Prime Air, which has struggled to transition to a fully operational service as Amazon founder Jeff Bezos predicted in 2013 that Amazon would be delivering goods weighing 5 pounds or less to customers’ doorsteps using drones within five years. During the Obama administration, Mullin, a former Marine Corps pilot, was responsible for Prime Air’s safety and compliance and ran sites in Oregon, California, and Texas.

As Prime Air was about to launch and begin delivering goods to consumers, CEO Andy Jassi, who will follow Bezos in 2021, announced the biggest layoff streak in the company’s history, including a significant layoff at Prime Air. Jassy’s cost-cutting policies were in response to a significant industry slowdown and investors moving away from technology as interest rates rose.

However, Prime Air’s troubles preceded the economic downturn. Regulations that restrict delivery locations hinder drones from operating. Even at two launch sites in Lockford, California, and College Station, Texas, shipments are still far from the 10,000 targets set by division chief David Carbon this year. Amazon claims hundreds of items have been delivered to these sites.

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