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A pair of well-known critics of President Trump achieved significant legal victories on the start of the week 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 maintained vehemently that they are not guilty, claiming that the administration and DOJ are simply targeting them for retaliation.

US District Judge Cameron Currie dismissed the charges against them due to prosecutor Lindsey Halligan's improper assignment as US attorney. But she also left open the possibility for the government to try again.

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

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

But the DOJ confronts steep obstacles to effectively try either after this defeat, and experts hesitate to predict what could happen next due to the unprecedented circumstances of the cases.

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

Could the justice department appeal?

The Department of Justice can challenge the judge's decision before a federal 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, pledging to use all available legal action, including an expedited appeal.

Previously, the former administration has aggressively appealed unfavourable rulings, taking cases from lower courts and sometimes fast-tracking its requests up to the Supreme Court.

Attorney Abbe Lowell, an attorney representing James, pledged to keep fighting any further politically driven indictments through all legal avenues.

In the event of an appeals process, the DOJ probably would have its own lawyers argue the case, making Halligan's role in the appeal uncertain.

Is it possible there be new charges?

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

Both pleaded not guilty. Besides claiming Halligan's appointment was invalid, both also asserted to be targets of retaliatory legal action.

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

As far as everything I've seen, a different attorney could present James's case to a new grand jury and secure a fresh indictment, said Professor Levine.

But legal expert John Day, head 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 strongly disputed, whether Comey's case can be re-indicted if a properly assigned attorney is assigned and is able to secure an charge.

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

It might be more difficult for the DOJ to try to bring the exact same charges against Comey.

A key issue is the statute of limitations – the time frame that government lawyers had to indict Comey for these specific allegations – which ended at the end of September. However, the dismissal of the charges would activate a half-year extension for the justice department to refile the case.

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

The ruling also suggests that since the charge is void, the statute of limitations has expired and there can be no further indictment, attorney Patrick Fitzgerald said on Monday.

What happens to Lindsey Halligan?

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

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

Therefore, Halligan had no lawful authority to present the indictment, the judge wrote.

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

This makes Halligan's role on future cases against both individuals, once more, unclear.

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

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

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