After two jetliner crashes killed 346 people, a $2.5 billion settlement that allowed Boeing (NYSE:BA) to avoid criminal prosecution failed to resolve questions about the safety of the aerospace giant’s planes.

Federal prosecutors now accuse the company of failing to live up to the terms of the 2021 settlement. Boeing has agreed to plead guilty to a felony fraud charge in a new deal with the Justice Department. The department hopes to file the detailed plea agreement Friday but says it may need “a few more days.”

Experts on corporate behavior say the effectiveness of the new agreement in improving safety may hinge on the power given to an independent monitor who will oversee Boeing for three years. Prosecutors required the appointment of such a monitor as a condition of the plea deal, which also includes a new $243.6 million fine.

“Your real concern is protecting against the loss of future lives in future crashes, and that is something that the monitor can have more impact on than simply the amount of the fine,” said John Coffee, a law professor at Columbia University who studies corporate governance and white-collar crime.

The finalized plea and sentence are due to be filed in U.S. District Court in Fort Worth, Texas. The filing will provide a more precise description of how the compliance monitor will be chosen and the scope of the monitor’s duties. The government appears to have backed away from a plan that would have given Boeing the biggest role in selecting the watchdog.

Families of some of the passengers who died in the crashes plan to oppose the agreement. They want a trial, not a plea deal, and argue that Boeing should pay a $24 billion fine. Paul Cassell, a lawyer for the families, said the relatives of crash victims should have the right to propose a monitor for the judge to appoint.

The Justice Department initially planned to select a monitor from a list of three nominees submitted by Boeing, and would ask the company for more names if necessary. However, a deal reached in principle a week later said the department would seek candidates through a public job posting on its website and then select one “with feedback from Boeing.” The extent of Boeing’s role remains unclear.

Once the department and Boeing settle on a choice, prosecutors will inform U.S. District Judge Reed O’Connor. If he doesn’t object within 10 days, the appointment will proceed. The selected monitor must meet “specific qualifications” outlined in the job posting and the department’s guidelines for selecting monitors in criminal cases.

The monitor will oversee Boeing’s compliance with the plea agreement during a three-year probation period and will write “a confidential annual report for the government,” filing an executive summary with the court.

The use of monitors as part of plea agreements with companies convicted of crimes reflects prosecutors’ reluctance to issue indictments and take cases to trial.

Brandon Garrett, a Duke University law professor who tracks criminal cases involving corporations, said prosecutors have long worried that a criminal indictment could destroy a large, publicly traded company, so they tended to favor out-of-court settlements in the most serious cases. That changed after the 2008 financial crisis, leading to concerns that companies were being treated as “too big to jail,” a phrase Garrett used in the title of his 2014 book.

The effectiveness of plea deals and deferred prosecution agreements that allow defendants—like Boeing in 2021—to avoid criminal liability has been questioned.

“Especially when you have companies repeatedly getting prosecuted, something needs to change — maybe these companies really should get a criminal record,” Garrett said. “That’s when we started to see more large cases where companies would be convicted.”

Nadia Milleron, whose 24-year-old daughter, Samya Stumo, died in the second of two fatal 737 Max crashes, said the Boeing plea deal is much better than the settlement reached three-and-a-half years ago. In January 2021, the Justice Department agreed not to prosecute the company for conspiring to defraud the U.S. government, a charge based on allegations that Boeing misled regulators who approved the 737 Max nearly a decade ago.

Still, Milleron and relatives of other crash victims want a trial to unearth more details about discussions inside Boeing leading up to, and following, the crashes, which occurred in 2018 in Indonesia and 2019 in Ethiopia.

It appeared likely that the Justice Department would permanently drop the 2021 charge until this January, when a panel covering an unused emergency exit blew off a Max jet during an Alaska Airlines flight. The Federal Aviation Administration increased its oversight, and the agency’s chief said manufacturing problems at Boeing “don’t seem to be getting resolved.”

The Justice Department defends its decision to seek a plea deal, stating it includes the most serious punishment possible under the charge facing Boeing.

“We should be asking whether these prosecutions are working and what can be done to make them more effective,” Garrett said. He suggested that the judge could take an active role in monitoring Boeing to ensure compliance with the new agreement after violating the old one.

Coffee, the Columbia law professor, said the key to whether the deal deters Boeing from future violations will be a strong and independent monitor.

“Companies fear a free agent roaming around in their files,” he said. “On the other hand, if there isn’t some ability for the monitor to directly go to the court and say ‘They are not living up to the terms of the agreement,’ you have an ineffective monitor.”

In one notorious case, prosecutors blocked a federal judge in New York from releasing a monitor’s reports about HSBC, a London-based bank that entered a deferred prosecution agreement over allegations that it failed to prevent a Mexican drug cartel from laundering money.

“I’m not saying we shouldn’t have deferred prosecution agreements, but they tend to be negotiated to be strongly in the interests of the defendant,” he said.

The judge in the Boeing case has indicated that after the Justice Department submits details of the plea agreement, he will give relatives of the victims seven days to lodge objections. The government and Boeing then will have 14 days to respond.

The January 2021 decision by the Justice Department not to prosecute Boeing came in the final days of the Trump administration. In 2022 and 2023, federal prosecutions of corporations rose modestly under the Biden administration, according to figures from the U.S. Sentencing Commission.

“We are in an election year, so we will be looking to see how that focus by the Department of Justice plays out after the election in November and whether the focus on corporate crime remains the same,” said Kya Henley, a former public defender in Maryland who now represents companies and individuals in white-collar cases. “Everyone gets to set their agenda.”

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