WASHINGTON (CN) – As they await trial on federal conspiracy charges stemming from the probe of Russian influence on last year’s election, former Trump campaign chairman Paul Manafort and his longtime business associate failed Thursday to secure looser bail conditions.

Manafort and Richard Gates returned to court this afternoon for the first time since turning themselves in Monday on a newly unsealed indictment.

U.S. Magistrate Judge Deborah Robinson had ordered the men released at the time on unsecured bonds of $10 million and $5 million, respectively, and prosecutors brought a pre-emptive motion that same day to keep those bonds in place.

Kevin Downing, an attorney for Manafort with the firm Miller Chevalier, lobbied to change the conditions in a nine-page document this morning.

Though the government characterizes Manafort as a flight risk, Downing said Manafort’s family obligations and his age make this fear “imagined.”

Shanlon Wu, an attorney for Gates with the firm Wu, Grohovsky and Whipple, filed a similar motion just minutes before Thursday’s proceedings.

U.S. District Court Judge Amy Berman Jackson complained at the hearing this afternoon about the timing and form of the filings, telling Wu that she had not been able to read his motion before taking her seat.

Saying she would not “rule on the fly from the bench,” Jackson instead directed the parties to file additional pleadings in the case.

“I think everybody needs to think through and talk through what their position is,” Jackson told the attorneys.

Despite not ruling on the issue, Jackson said she was “very concerned” that the unsecured bond placed on Manafort and Gates is not sufficient.

Jackson did allow Wu to file paperwork with pretrial services that would allow Gates to travel to a sports tournament in which his child will compete over the weekend.

A pretrial services representative said in court Gates would need to alert her office of the time he was planning on leaving his house for the tournament, as well as its location and the time he would return to his house.

Apart from the bond issues, Jackson also asked the parties to file briefs about a potential gag order she is considering to keep the attorneys from speaking publicly about the case.

“This is a criminal trial, it is not a public-relations campaign,” Jackson said in court Thursday.

Manafort and Gates pleaded not guilty Monday to the 12-count indictment accusing them of money laundering and conspiracy charges.

Representatives for Special Prosecutor Robert Mueller say they are using a “novel theory” of the Foreign Agent Registration Act to prosecute the case. Only used six times since 1966, the law has resulted just one conviction.

Manafort and Gates are charged with hiding money they earned from lobbying for a pro-Russian Ukrainian political party overseas to avoid taxes in the United States.

The pair are due back in court on Monday at 9:30 for a bond review hearing.