Republican operative and Trump associate Roger Stone Roger Jason StoneThe agony of justice Our Constitution is under attack by Attorney General William Barr Justice IG investigating Stone sentencing: report MORE found himself in more legal trouble Friday after a federal judge demanded an explanation as to why he did not disclose the “imminent” publication of a book that may violate a gag order.

U.S. District Court Judge Amy Berman Jackson imposed the gag order last week after Stone posted a picture on his Instagram page that put crosshairs over Jackson’s head.

The gag prohibits Stone from discussing his case in public, including criticizing Jackson or special counsel Robert Mueller Robert (Bob) MuellerCNN's Toobin warns McCabe is in 'perilous condition' with emboldened Trump CNN anchor rips Trump over Stone while evoking Clinton-Lynch tarmac meeting The Hill's 12:30 Report: New Hampshire fallout MORE, which the book reportedly does.

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“It is FURTHER ORDERED that defendant shall file an additional submission by March 4, 2019 identifying the specific date of the ‘imminent general rel[e]ase’ of the book … and explaining why this matter -- which was known to the defendant -- was not brought to the Court's attention,” Jackson wrote in Friday’s court order.

Jackson noted that Stone’s lawyers could have informed her of the book multiple times throughout February. She also said when she imposed the gag order that she had “serious doubts whether [Stone] learned any lesson at all,” and said she would consider sending Stone to jail for future transgressions.

Stone has pleaded not guilty to charges of lying to Congress and obstructing justice. He first drew the scrutiny of Mueller over his alleged coordination with WikiLeaks regarding the dumping of a slew of Democratic documents in 2016 meant to embarrass Democratic presidential nominee Hillary Clinton Hillary Diane Rodham ClintonButtigieg stands in as Pence for Harris's debate practice Senate GOP sees early Supreme Court vote as political booster shot Poll: 51 percent of voters want to abolish the electoral college MORE. Mueller said in a court filing Friday he expects it will take five to eight days for the government to lay out its case against the Trump associate.

Stone is now out of custody and was released on an unsecured personal recognizance bond. He is allowed to travel between South Florida, Washington and New York City.

Despite the gag order, Stone is allowed to continue his online fundraising for his legal defense and speak on other matters.