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Two well-known critics of President Trump obtained significant legal victories on Monday when a federal judge dismissed the federal indictments against them.

Over recent weeks since their indictments, former FBI Director James Comey and New York Attorney General Letitia James have insisted vehemently that they are not guilty, asserting that the president and justice department are merely targeting them for revenge.

Federal Judge Cameron Currie tossed the indictments against them due to prosecutor Lindsey Halligan's invalid appointment as US attorney. However, she left the door open for the government to refile the case.

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Comey acknowledged that likelihood after the ruling, saying he thinks Trump will probably target him once more.

And White House spokesperson Abigail Jackson seemed to confirm it: This will not be the last chapter on this matter.

But the government faces significant obstacles to successfully prosecute both after this setback, and experts are reluctant to forecast what could happen next due to the unprecedented circumstances of the cases.

It feels to me like uncharted territory, said Kay Levine, Emory University School of Law professor.

Could the DOJ challenge the ruling?

The Department of Justice can contest Judge Currie's ruling 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, vowing to use all legal means, including an immediate 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.

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

If there is an appeals process, the justice department likely would have its own lawyers present the arguments, making Halligan's involvement in the appeals process unclear.

Could there be new charges?

The government charged Comey with making false statements to Congress and obstructing justice. Federal prosecutors charged James with bank fraud and making false statements to a bank.

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

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

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

But legal expert John Day, head of the American College of Trial Lawyers, said it could be a complex process – especially in the Comey matter.

It's clear that it will be hotly contested, whether Comey's case can be re-indicted if a properly assigned attorney is assigned and is able to secure an indictment.

He characterized the tangle of attorneys, judges, and motions involved as a procedural morass with no easy solutions.

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

A key issue is the legal time limit – the deadline that government lawyers had to charge him for these particular claims – which expired at the close of September. Nonetheless, the indictment's dismissal would activate a half-year extension for the justice department to refile the case.

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

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

What is the fate of Lindsey Halligan?

In the pair of rulings on the charges against James and Comey, the judge was direct: Halligan was wrongly appointed.

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

Therefore, she had no lawful authority to file the charges, she wrote.

Federal prosecutors are nominated by the US president and need Senate approval. Federal statutes regulate how people can be assigned on a temporary basis, but Judge Currie found that Halligan's appointment had breached these regulations.

That leaves Halligan's role on subsequent cases against James and Comey, again, uncertain.

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

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

The White House maintained its position that Halligan was lawfully appointed, press secretary Karoline Leavitt told reporters on Monday.