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A pair of well-known critics of former President Trump obtained major court wins on Monday when a US 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 not guilty, asserting that the administration and DOJ are merely singling out them for retaliation.

US District Judge Cameron Currie tossed the charges against them due to attorney Lindsey Halligan's improper assignment as US attorney. However, she left open the possibility for the federal authorities to try again.

• Court throws out charges against ex-FBI director Comey and New York AG James
• Federal judge states DOJ errors may have tainted the Comey trial
• What are former FBI head James Comey charged with?

Comey acknowledged that likelihood after the ruling, saying he thinks Trump is likely to come after him once more.

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

But the government faces significant hurdles to effectively try either after this setback, and legal analysts are reluctant to forecast what could happen next due to the cases' unprecedented nature.

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 higher appeals court. In this case, that would be the Fourth Circuit Court of Appeals.

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

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

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

If there is an appeals process, the justice department likely would have its own attorneys argue the case, making Halligan's involvement in the appeals process unclear.

Is it possible there be fresh indictments?

The government charged James Comey with lying to Congress and obstructing justice. Government lawyers charged Letitia James with financial fraud and providing false information to a financial institution.

Each pleaded not guilty. Besides arguing 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 assemble new grand juries and secure 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 John Day, head of the American College of Trial Lawyers, said it could be a complicated path – certainly in the Comey matter.

It's clear that it will be hotly contested, whether Mr Comey's case can be re-indicted if a lawfully appointed prosecutor is assigned and is able to secure an charge.

He characterized the complex web of lawyers, courts, and legal filings involved as a legal quagmire with no simple answers.

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

A key issue is the legal time limit – the time frame that prosecutors had to charge Comey for these particular claims – which ended at the end of September. However, the dismissal of the charges would trigger a six-month grace period for the DOJ to bring the case again.

Even so in that case, his legal team said it plans to argue the prosecution is out of time.

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

What is the fate of prosecutor Lindsey Halligan?

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

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

As a result, Halligan had no lawful authority to file the charges, she wrote.

US attorneys are nominated by the US president and require Senate approval. Federal statutes regulate how people can be appointed on a interim basis, but Judge Currie found that Halligan's assignment had violated these laws.

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

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

But Bondi said on that day that she designated her a special US attorney and commended her work as outstanding.

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