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Two well-known critics of former President Trump obtained significant legal victories on Monday when a federal judge dismissed the government's charges filed against them.

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

US District Judge Cameron Currie dismissed the charges in their cases due to attorney Lindsey Halligan's improper assignment as federal prosecutor. But she also left the door open for the government to try again.

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Comey acknowledged that possibility after the decision, saying he believes Trump will probably come after him once more.

And White House spokesperson Abigail Jackson appeared to agree: This will not be the final word on this issue.

But the government faces steep obstacles to successfully prosecute either after this setback, and legal analysts are reluctant to predict what could happen next due to the unprecedented circumstances of the cases.

In my view, it's uncharted territory, said Kay Levine, law professor at Emory University.

Could the DOJ challenge the ruling?

The Department of Justice can challenge Judge Currie's ruling before a federal appeals court. In this case, that would be the Fourth Circuit Appeals Court.

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

In other cases, the Trump administration has strongly challenged adverse decisions, moving cases from lower courts and sometimes fast-tracking its petitions up to the US Supreme Court.

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

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

Is it possible there be fresh indictments?

The government accused James Comey with lying to lawmakers and obstruction of justice. Federal prosecutors charged Letitia James with bank fraud and providing false information to a bank.

Each entered not guilty pleas. In addition to claiming Halligan was unlawfully appointed, both also claimed to be targets of vindictive prosecution.

With the original indictments thrown out (although appeals might alter this), the DOJ might try to convene fresh grand juries and secure new charges.

Based on my analysis, a different attorney could present James's case to a different grand jury and secure a new indictment, said Ms Levine.

But legal expert John Day, president of the American College of Trial Lawyers, said it could be a complicated path – certainly in Comey's case.

It's clear that 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 charge.

He described the tangle of lawyers, courts, and motions involved as a legal quagmire with no simple answers.

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

A key issue is the statute of limitations – the deadline that prosecutors had to indict Comey for these specific allegations – which ended at the end of September. Nonetheless, the dismissal of the charges would trigger a six-month grace period for the DOJ to bring the case again.

Still in that case, his legal team said it intends to contend the government is past the deadline.

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

What happens to prosecutor Lindsey Halligan?

In both decisions on the charges against James and Comey, Judge Currie was direct: Halligan's appointment was improper.

The judge stated in the James ruling that the AG's effort to install Ms. Halligan as Acting US Attorney for the Virginia Eastern District was invalid.

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

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

This makes Halligan's role on future cases against James and Comey, once more, unclear.

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

But Attorney General Bondi said on that day that she designated Halligan a special federal prosecutor and praised her work as outstanding.

The administration stood by its stance that Halligan's appointment was legal, press secretary Karoline Leavitt told the press on Monday.