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A pair of prominent critics of President Trump obtained major legal victories on Monday when a federal judge dismissed the federal indictments against them.

For weeks following their charges, former FBI Director James Comey and NY AG Letitia James have insisted vehemently that they are innocent, claiming that the administration and DOJ are simply targeting them for revenge.

Federal Judge Cameron Currie dismissed the indictments in their cases due to prosecutor Lindsey Halligan's invalid appointment as federal prosecutor. However, she left open the possibility for the federal authorities to try again.

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Comey acknowledged that possibility after the ruling, stating he thinks the former president will probably come after him again.

And White House spokeswoman Abigail Jackson seemed to confirm it: This isn't the last chapter on this matter.

But the DOJ faces steep obstacles to successfully prosecute both after this setback, and legal analysts hesitate to predict what could happen next due to the unprecedented circumstances of the cases.

It feels to me like uncharted territory, stated Kay Levine, law professor at Emory University.

Might the DOJ appeal?

The Department of Justice can challenge Judge Currie's ruling before a higher 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 expedited appeal.

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

Attorney Abbe Lowell, James's lawyer, vowed to continue to challenge any further politically driven indictments 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 appeal unclear.

Could there be fresh indictments?

The government accused James Comey with making false statements to lawmakers and obstruction of justice. Federal prosecutors indicted James with bank fraud and making false statements to a bank.

Both pleaded not guilty. In addition to claiming Halligan was unlawfully appointed, they also asserted to be victims of vindictive prosecution.

Since the initial charges were dismissed (although appeals might alter this), the DOJ might try to convene new grand juries and secure new charges.

Based on my analysis, a new prosecutor could bring James' case to a different grand jury and secure a fresh indictment, stated Professor Levine.

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

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

He described the tangle of attorneys, judges, and legal filings involved as a procedural morass with no simple answers.

It could be harder for the government to try to file the identical accusations against James Comey.

One problem is the legal time limit – the time frame that government lawyers had to indict Comey for these specific allegations – which ended at the close of September. However, the dismissal of the charges would trigger a six-month grace period for the justice department to bring the case again.

Even so in that case, his legal team said it intends to contend the government is out of time.

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

What happens to Lindsey Halligan?

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

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

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

US attorneys are proposed by the US president and require Senate approval. US laws regulate how individuals 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 both individuals, once more, unclear.

The ruling also could cast a shadow on any other cases Halligan has brought in the Virginia Eastern District where she serves.

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

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