The contract between Boeing and the International Association of Machinists is due to expire at 11:59 pm PT on September 12. Without a new contract, the workers who build its planes in Washington state are set to start the first strike at the company in 16 years. And right now, the chances of a deal don’t look good, according to the head of the union local.

“We’re far apart is on all the main issues — wages, health care, retirement, time off,” Jon Holden, president of IAM District 751, told CNN this past week. “We continue to work through that, but it’s been a tough slog to get through.”

It’s just the latest in a series of serious and high-profile problems at a company that has dealt with fatal crashes traced to a design flaw in its best-selling jet, accusations that it put profits and production speed ahead of quality and safety, tanking aircraft sales, an agreement to plead guilty to criminal charges that it deceived regulators, and massive financial losses covered by soaring levels of debt.

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The company said that wages for IAM members have increased 60% over the last 10 years due to general wage increases, cost-of-living adjustments and incentive pay. But the union is still angry over the earlier concessions. It is also seeking improved time off and also better job guarantees so it won’t be faced once again with the threat of losing work to nonunion plants.

“We cannot go through another period where a year or two from now where our jobs are threatened,” Holden said,

Numerous unions, including the Teamsters at UPS and the United Auto Workers union at GM, Ford and Stellantis, won double-digit wage increases in recent union deals. But in those and many other cases, they were negotiating with companies making record profits and with plenty of resources to satisfy union demands.

By contrast, the problems at Boeing have resulted in $33.3 billion in core operating losses over the course of the last five years, forcing the company to go deeply into debt. It is in danger of having that debt downgraded to junk bond status, but Holden insists that the union still has leverage in these talks.