Originally Published: 07 AUG 23 11:37 ET

By Katelyn Polantz, CNN Reporter, Crime and Justice

(CNN) — Judge Aileen Cannon is asking the Justice Department and Donald Trump co-defendant Walt Nauta to weigh in on the legality of special counsel Jack Smith’s ongoing grand jury activity in Washington, DC, which relates to the obstruction portion of the Mar-a-Lago documents case before her in Florida.

In an order Monday, Cannon said Nauta’s lawyers “shall address the legal propriety of using an out-of-district grand jury proceeding to continue to investigate and/or to seek post-indictment hearings on matters pertinent to the instant indicted matter in this district” by August 17. The special counsel must reply by August 22.

The special counsel previously told Cannon that “the grand jury in this district [in Florida] and a grand jury in the District of Columbia continued to investigate further obstructive activity,” which resulted in the latest group of criminal charges before her against Trump, Nauta and a third defendant, Mar-a-Lago employee Carlos De Oliveira.

Nauta’s attorneys have also been told to respond to questions the Justice Department has raised about their possible conflicts for representing multiple people in the probe in addition to Nauta. The Justice Department previously flagged to Cannon the possibility of a conflict of interest because Nauta’s lawyer Stanley Woodward has represented others who are likely to be witnesses against him and Trump at trial.

Cannon’s schedule indicates the possible conflict issue won’t be resolved for at least two weeks.

Woodward’s representation of Trump IT employee and witness Yuscil Taveras was moved to another lawyer after a recent proceeding before the chief federal judge in Washington, CNN has confirmed. Taveras had been represented by the same attorney as Nauta, but received a target letter after the June indictment of Trump and Nauta. Taveras, under a new lawyer’s representation, then spoke to investigators.

Woodward represents at least one additional possible trial witness in the Florida documents case, as well as several others in Trump’s circles and related to the January 6 investigation, and his work for them is funded by Trump’s Save America PAC.

Trump now faces 40 felony counts, alleging he illegally retained national defense information and that he concealed documents in violation of witness-tampering laws in the Justice Department’s probe into the materials. He Trump and Nauta have pleaded not guilty to all charges. De Oliveira is set to be arraigned on Thursday.