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Two well-known opponents of former President Trump secured major court wins on Monday when a federal judge dismissed the federal indictments 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 innocent, asserting that the administration and DOJ are merely targeting them for retaliation.

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

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

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

But the DOJ confronts significant obstacles to successfully prosecute either after this setback, and experts are reluctant to predict what could happen next due to the unprecedented circumstances of the cases.

It feels to me like unexplored legal ground, stated Kay Levine, Emory University School of Law professor.

Could the justice department appeal?

The DOJ can challenge 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 take this route, pledging to use all legal means, including an expedited appeal.

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

Abbe Lowell, an attorney representing James, pledged to continue to challenge any additional politically driven indictments through all legal avenues.

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

Could there be fresh indictments?

The government charged Comey with lying to Congress and obstructing justice. Federal prosecutors charged Letitia James with financial fraud and providing false information to a bank.

Each pleaded not guilty. Besides claiming Halligan was unlawfully appointed, they also claimed to be targets of retaliatory legal action.

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

As far as everything I've seen, a new prosecutor could bring James' case to a new grand jury and secure a new indictment, said Professor Levine.

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

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

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

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

One problem is the statute of limitations – the time frame that government lawyers had to charge Comey for these particular claims – which ended at the end of September. However, the indictment's dismissal would trigger a half-year extension for the justice department to refile the case.

Even so in that case, his legal team said it plans to argue the government is past the deadline.

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 on Monday.

What is the fate of Lindsey Halligan?

In both decisions on the indictments against Comey and James, the judge was blunt: Halligan was wrongly appointed.

The judge stated in the James ruling that the Attorney General's attempt to appoint Halligan as Interim US Attorney for the Eastern District of Virginia was invalid.

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

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

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

The decision might also cast a shadow on other cases Halligan has prosecuted in the Virginia Eastern District where she works.

But Attorney General Bondi said on that day that she made her a special US attorney and praised her work as outstanding.

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