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Two prominent critics of President Trump obtained major court wins on Monday when a federal judge dismissed the government's charges filed against them.

For weeks since their indictments, ex-FBI chief James Comey and New York Attorney General Letitia James have argued fiercely that they are not guilty, claiming that the administration and DOJ are merely targeting them for revenge.

Federal Judge Cameron Currie dismissed the charges against them due to attorney Lindsey Halligan's improper appointment as US attorney. However, she left open the possibility for the government to try again.

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Comey admitted that likelihood after the ruling, saying he thinks the former president will probably come after him once more.

And White House spokeswoman Abigail Jackson appeared to agree: This will not be the last chapter on this issue.

But the DOJ faces significant obstacles to effectively try both after this setback, and experts hesitate to predict what could occur next due to the cases' unprecedented nature.

It feels to me like unexplored legal ground, stated Professor Kay Levine, law professor at Emory University.

Could the DOJ challenge the ruling?

The Department of Justice can challenge 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 indicated she would pursue this option, pledging to use all available legal action, including an immediate appeal.

In other cases, the Trump administration has aggressively appealed unfavourable rulings, moving cases from lower courts and sometimes fast-tracking its requests up to the US Supreme Court.

Abbe Lowell, an attorney representing James, pledged to keep fighting any further politically motivated charges through all legal avenues.

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

Is it possible there be fresh indictments?

The federal prosecutors accused Comey with making false statements to lawmakers and obstructing justice. Federal prosecutors charged Letitia James with financial fraud and providing false information to a bank.

Both entered not guilty pleas. Besides arguing Halligan's appointment was invalid, they also claimed to be victims of vindictive prosecution.

Since the initial charges were dismissed (though, of course, appeals could change that), the government might try to assemble new grand juries and obtain new charges.

Based on my analysis, 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 complicated path – especially in the Comey matter.

I can tell you it will be hotly contested, whether Mr Comey's case can be re-indicted if a properly assigned attorney is assigned and is can obtain an charge.

He characterized the complex web of lawyers, judges, and motions involved as a procedural morass with no easy solutions.

It could be more difficult for the DOJ to try to bring the identical accusations against Comey.

A key issue is the legal time limit – the time frame that government lawyers had to charge Comey for these particular claims – which ended at the close of September. However, the dismissal of the charges would activate a six-month grace period for the justice department to refile the case.

Still in that case, his lawyers said it plans to contend the government is past the deadline.

The ruling also suggests that since the indictment is void, the time limit has expired and there can be no new indictment, lawyer Patrick Fitzgerald said on Monday.

What is the fate of Lindsey Halligan?

In both decisions on the charges against Comey and James, Judge Currie was direct: Halligan was wrongly appointed.

Judge Currie wrote in the James ruling that the AG's effort to appoint Halligan as Interim US Attorney for the Eastern District of Virginia was unlawful.

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

Federal prosecutors are nominated by the president and need Senate approval. US laws govern how individuals can be assigned on a temporary basis, but Judge Currie found that Halligan's assignment had breached these laws.

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

The decision might also raise doubts on other cases Halligan has prosecuted in the Eastern District of Virginia where she serves.

But Attorney General Bondi said on Monday that she designated her a special federal prosecutor and commended her work as excellent.

The administration maintained its position that Halligan's appointment was legal, spokesperson Karoline Leavitt told the press on Monday.