Boeing is seeking to raise some $19bn (€17.56bn) through a share sale, in the hope of boosting liquidity as its workers continue strike action that has lasted for more than a month.
In a statement issued on Monday, the aircraft manufacturer said it would offer 90 million common shares, estimated to be worth around $14bn (€12.94bn).
It added that $5bn (€4.62bn) will be raised through depositary shares.
The company said it plans to use the net proceeds for general corporate purposes, which may include repaying debt, additions to working capital, capital expenditures, and funding and investments in its subsidiaries.
Securing extra cash is a top priority for the company's new Chief Executive Officer Kelly Ortberg, who began his role at Boeing in August.
There is fear that a wave of scandals, strikes and operational problems at the company could soon result in a credit rating downgrade.
Boeing workers have now been striking since September over stagnant wages and pension and healthcare rights.
The industrial action is thought to be costing Boeing around $50m (€46.22m) a day.
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Last week Boeing factory workers voted to reject the company's latest contract offer - meaning the strike will continue.
Local union leaders in Seattle said 64% of members of the International Association of Machinists and Aerospace Workers who cast ballots voted against accepting the contract offer.
The labour standoff comes during an already challenging year for Boeing, which became the focus of multiple federal investigations after a door panel blew off a 737 Max plane during an Alaska Airlines flight in January.
The strike has deprived the company of much-needed cash that it gets from delivering new planes to airlines.
On Wednesday, the company reported a third-quarter loss of more than $6bn (€5.55bn).
Boeing hasn't had a profitable year since 2018, and Wednesday's numbers represented the second-worst quarter in the manufacturer's history.
The company burned nearly $2bn (€1.85bn) in cash in the quarter, weakening its balance sheet, which is loaded down with $58bn (€53.61bn) in debt.
Chief Financial Officer Brian West said the company will not generate positive cash flow until the second half of next year.
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