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Two well-known critics of former President Trump obtained major court wins on Monday when a US judge threw out the federal indictments against them.

For weeks since their indictments, ex-FBI chief James Comey and NY AG Letitia James have insisted fiercely that they are not guilty, claiming that the president and justice department are merely singling out them for retaliation.

Federal Judge Cameron Currie tossed the charges in their cases due to attorney Lindsey Halligan's improper appointment as US attorney. But she also left the door open for the federal authorities to try again.

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Comey admitted that likelihood after the ruling, saying he thinks Trump will probably come after him again.

And White House spokeswoman Abigail Jackson seemed to confirm it: This isn't the final word on this issue.

But the DOJ faces significant obstacles to successfully prosecute either after this setback, and experts are reluctant to forecast what could occur next due to the cases' unprecedented nature.

In my view, it's uncharted territory, said Professor Kay Levine, Emory University School of Law professor.

Could the DOJ challenge the ruling?

The Department of Justice can contest the judge's decision before a federal appeals court. In this case, that would be the Fourth Circuit Court of Appeals.

US Attorney General Pam Bondi signaled she would pursue this option, pledging to use all available legal action, including an expedited appeal.

In other cases, the Trump administration has aggressively appealed adverse decisions, moving cases from trial courts and sometimes accelerating its requests up to the Supreme Court.

Abbe Lowell, James's lawyer, vowed to keep fighting any further politically driven indictments through every lawful means available.

In the event of an appeals process, the DOJ likely would have its own attorneys present the arguments, making Halligan's involvement in the appeal unclear.

Is it possible there be new charges?

The government accused James Comey with lying to Congress and obstructing justice. Federal prosecutors charged Letitia James with financial fraud and making false statements to a financial institution.

Both pleaded not guilty. In addition to arguing Halligan's appointment was invalid, they also asserted to be targets of retaliatory legal action.

With the original indictments thrown out (although appeals might alter this), the government might try to assemble new grand juries and secure new indictments.

As far as everything I've seen, a new prosecutor could bring James' case to a different grand jury and get a fresh indictment, said Ms Levine.

But John Day, head of the American College of Trial Lawyers, said it could be a complex process – certainly in Comey's case.

I can tell you it will be strongly disputed, whether Comey's case can be recharged if a properly assigned attorney is appointed and is able to secure an indictment.

He characterized the complex web of attorneys, judges, and legal filings involved as a legal quagmire with no easy solutions.

It might be harder for the government to try to bring the exact same charges against James Comey.

A key issue is the statute of limitations – the time frame that government lawyers had to indict him for these particular claims – which ended at the end of September. However, the dismissal of the charges would trigger a half-year extension for the DOJ to refile the case.

Still in that situation, his legal team said it intends to argue the prosecution is out of time.

The ruling also suggests that since the charge is invalid, the statute of limitations has run and there can be no new indictment, lawyer Patrick Fitzgerald said Monday.

What is the fate of prosecutor Lindsey Halligan?

In the pair of rulings on the charges against James and Comey, Judge Currie was blunt: Halligan was wrongly appointed.

The judge stated in the James decision that the AG's effort to appoint Halligan as Interim US Attorney for the Virginia Eastern District was invalid.

As a result, Halligan had no lawful authority to file the charges, she wrote.

Federal prosecutors are proposed by the president and need US Senate confirmation. Federal statutes regulate how people can be assigned on a interim basis, but the judge determined that Halligan's assignment had violated these laws.

That leaves Halligan's position on subsequent cases against James and Comey, once more, uncertain.

The ruling also could cast a shadow on other cases Halligan has prosecuted in the Eastern District of Virginia where she works.

But Attorney General Bondi said on Monday that she designated her a special US attorney and commended her work as outstanding.

The administration maintained its position that Halligan was lawfully appointed, press secretary Karoline Leavitt told the press on Monday.