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Two prominent critics of President Trump achieved significant court wins on Monday when a federal judge dismissed the federal indictments filed against them.

Over recent weeks following their charges, former FBI Director James Comey and NY AG Letitia James have maintained 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 indictments against them due to prosecutor Lindsey Halligan's improper assignment as federal prosecutor. However, she left open the possibility for the government to try again.

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Comey acknowledged that likelihood after the decision, stating he thinks Trump will probably target him again.

And White House spokesperson Abigail Jackson appeared to agree: This isn't the last chapter on this matter.

But the DOJ confronts significant hurdles to successfully prosecute both after this setback, and legal analysts are reluctant to forecast what could occur next due to the cases' unprecedented nature.

It feels to me like unexplored legal ground, said Kay Levine, Emory University School of Law professor.

Might the DOJ challenge the ruling?

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

US Attorney General Pam Bondi signaled she would pursue this option, vowing to use all legal means, including an immediate appeal.

In other cases, the former administration has strongly challenged unfavourable rulings, moving cases from lower courts and sometimes accelerating its petitions up to the Supreme Court.

Attorney Abbe Lowell, an attorney representing James, pledged to keep fighting any further politically driven indictments through every lawful means available.

In the event of an appeal, the DOJ likely would have its own attorneys argue the case, making Halligan's role in the appeal unclear.

Is it possible there be fresh indictments?

The federal prosecutors charged James Comey with lying to lawmakers and obstruction of justice. Federal prosecutors charged James with financial fraud and making false statements to a bank.

Both entered not guilty pleas. Besides claiming Halligan was unlawfully appointed, both also asserted to be targets of retaliatory legal action.

Since the initial charges were dismissed (although appeals might alter this), the government might try to assemble new grand juries and obtain new charges.

Based on my analysis, a new prosecutor could present James's case to a different grand jury and get a new indictment, stated Ms Levine.

But legal expert 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 strongly disputed, whether Mr Comey's case can be re-indicted if a lawfully appointed prosecutor is appointed and is able to secure an indictment.

He described the tangle of lawyers, courts, and motions involved as a procedural morass with no easy solutions.

It could be more difficult for the DOJ to try to file the exact same charges against Comey.

A key issue is the statute of limitations – the time frame that prosecutors had to indict Comey for these specific allegations – which ended at the close of September. Nonetheless, the indictment's dismissal would trigger a half-year extension for the DOJ to refile the case.

Even so in that case, his lawyers said it intends to argue the government is out of time.

The decision further indicates that because the indictment is void, the statute of limitations has expired and there can be no further indictment, lawyer Patrick Fitzgerald said Monday.

What happens to prosecutor Lindsey Halligan?

In the pair of rulings on the indictments against James and Comey, the judge was blunt: Halligan's appointment was improper.

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

As a result, she lacked legal power to file the charges, she wrote.

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

That leaves Halligan's position on future cases against both individuals, again, unclear.

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

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

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