In one of the most important cases of the social media age, free speech and national security collide at the Supreme Court on Friday in arguments over the fate of TikTok, a wildly popular digital platform that roughly half the people in the United States use for entertainment and information.

TikTok says it plans to shut down the social media site in the U.S. by Jan. 19 unless the Supreme Court strikes down or otherwise delays the effective date of a law aimed at forcing TikTok’s sale by its Chinese parent company.

Working on a tight deadline, the justices also have before them a plea from President-elect Donald Trump, who has dropped his earlier support for a ban, to give him and his new administration time to reach a “political resolution” and avoid deciding the case. It’s unclear if the court will take the Republican president-elect’s views — a highly unusual attempt to influence a case — into account.

TikTok and China-based ByteDance, as well as content creators and users, argue the law is a dramatic violation of the Constitution’s free speech guarantee.

“Rarely if ever has the court confronted a free-speech case that matters to so many people,” lawyers for the users and content creators wrote. Content creators are anxiously awaiting a decision that could upend their livelihoods and are eyeing other platforms.

The case represents another example of the court being asked to rule about a medium with which the justices have acknowledged they have little familiarity or expertise, though they often weigh in on meaty issues involving restrictions on speech.

The Biden administration, defending the law that President Joe Biden signed in April after it was approved by wide bipartisan majorities in Congress, contends that “no one can seriously dispute that (China’s) control of TikTok through ByteDance represents a grave threat to national security.”

Officials say Chinese authorities can compel ByteDance to hand over information on TikTok’s U.S. patrons or use the platform to spread or suppress information.

But the government “concedes that it has no evidence China has ever attempted to do so,” TikTok told the justices, adding that limits on speech should not be sustained when they stem from fears that are predicated on future risks.

In December, a panel of three appellate judges, two appointed by Republicans and one by a Democrat, unanimously upheld the law and rejected the First Amendment speech claims.

Adding to the tension, the court is hearing arguments just nine days before the law is supposed to take effect and 10 days before a new administration takes office.

In language typically seen in a campaign ad rather than a legal brief, lawyers for Trump have called on the court to temporarily prevent the TikTok ban from going into effect but refrain from a definitive resolution.

“President Trump alone possesses the consummate dealmaking expertise, the electoral mandate, and the political will to negotiate a resolution to save the platform while addressing the national security concerns expressed by the Government — concerns which President Trump himself has acknowledged,” D. John Sauer, Trump’s choice to be his administration’s top Supreme Court lawyer, wrote in a legal brief filed with the court.

Trump took no position on the underlying merits of the case, Sauer wrote. Trump’s campaign team used TikTok to connect with younger voters, especially male voters, and Trump met with TikTok CEO Shou Zi Chew at Trump’s Mar-a-Lago club in Palm Beach, Florida, in December. He has 14.7 million followers on TikTok.

The justices have set aside two hours for arguments, and the session likely will extend well beyond that. Three highly experienced Supreme Court lawyers will be making arguments. Solicitor General Elizabeth Prelogar will present the Biden administration’s defense of the law, while Trump’s solicitor general in his first administration, Noel Francisco, will argue on behalf of TikTok and ByteDance. Stanford Law professor Jeffrey Fisher, representing content creators and users, will be making his 50th high court argument.

If the law takes effect, Trump’s Justice Department will be charged with enforcing it. Lawyers for TikTok and ByteDance have argued that the new administration could seek to mitigate the law’s most severe consequences.

But they also said that a shutdown of just a month would cause TikTok to lose about one-third of its daily users in the U.S. and significant advertising revenue.

President-elect Donald Trump is asking the Supreme Court to call off Friday’s sentencing in his hush money case in New York.

Trump’s lawyers turned to the nation’s highest court on Wednesday after New York courts refused to postpone the sentencing by Judge Juan M. Merchan, who presided over Trump’s trial and conviction last May on 34 felony counts of falsifying business records. Trump has denied wrongdoing.

The justices asked for a response from prosecutors by Thursday morning. Trump’s team sought an immediate stay of the scheduled sentencing, saying it would wrongly restrict him as he prepares to take office. While Merchan has indicated he will not impose jail time, fines or probation, Trump’s lawyers argued a felony conviction would still have intolerable side effects.

The sentencing should be delayed as he appeals the conviction to “prevent grave injustice and harm to the institution of the Presidency and the operations of the federal government,” they argued.

The emergency motion is from lawyers John Sauer, Trump’s pick for solicitor general, who represents the government before the high court, and Todd Blanche, in line to be the second-ranking official at the Justice Department.

They also pointed to the Supreme Court ruling giving Trump and other presidents broad immunity from prosecutions over their actions in office, saying it supports their argument that his New York conviction should be overturned.

Their filing said the New York trial court “lacks authority to impose sentence and judgment on President Trump — or conduct any further criminal proceedings against him— until the resolution of his underlying appeal raising substantial claims of Presidential immunity, including by review in this Court if necessary.”

The Republican president-elect’s spokesman, Steven Cheung, called for the case to be dismissed in a statement. Trump simultaneously filed an emergency appeal in front of New York’s highest court.

The Manhattan district attorney’s office, meanwhile, said it will respond in court papers. Trump’s convictions arose from what prosecutors said was an attempt to cover up a $130,000 hush money payment to porn actor Stormy Daniels just before the 2016 presidential election.

Daniels claims she had a sexual encounter with Trump in 2006. He denies it.

The Supreme Court’s immunity opinion came in a separate election interference case against him, but Trump’s lawyers say it means some of the evidence used against him in his hush money trial should have been shielded by presidential immunity. That includes testimony from some White House aides and social media posts made while he was in office.

Merchan has disagreed, finding they would qualify as personal business. The Supreme Court’s immunity decision was largely about official acts of presidents while in office.

Rudy Giuliani was found in contempt of court Monday for failing to properly respond to requests for information as he turned over assets to satisfy a $148 million defamation judgment granted to two Georgia election workers.

Judge Lewis J. Liman ruled after hearing Giuliani testify for a second day at a contempt hearing called after lawyers for the election workers said the former New York City mayor had failed to properly comply with requests for evidence over the last few months.

Liman said Giuliani “willfully violated a clear and unambiguous order of this court” when he “blew past” a Dec. 20 deadline to turn over evidence that would help the judge decide at a trial later this month whether Giuliani can keep a Palm Beach, Florida, condominium as his residence or must turn it over because it is deemed a vacation home.

Because Giuliani failed to reveal the full names of his doctors, a complete list of them, or of his other professional services providers, the judge said he will conclude at trial that none of them were in Florida or had been changed after Jan. 1, 2024. That was the date Giuliani says he established Palm Beach as his permanent residence.

Liman also excluded Giuliani from offering testimony about emails or text messages to establish that his homestead was in Florida.

The judge said Giuliani produced only a dozen and a half “cherry picked” documents and no phone records, emails or texts related to his homestead. He said he can also make inferences during the trial about “gaps” in evidence that resulted from Giuliani’s failure to turn over materials.

Liman said he would withhold judgment on other possible sanctions.

On Friday, Giuliani testified for about three hours in Liman’s Manhattan courtroom, but the judge permitted him to finish testifying remotely on Monday for over two hours from his Palm Beach condominium. By the time the judge issued his oral ruling, Giuliani was no longer present at all.

Joseph Cammarata, Giuliani’s attorney, noted in an email afterward that the election workers were not in the courtroom either and he called the outcome “no surprise.”

“This case is about lawfare and the weaponization of the legal system in New York City,” he said.

Cammarata said the state criminal case against President-elect Donald Trump and the civil litigation against Giuliani were “very similar. It’s the left wing Democrats trying to use liberal Judges in New York to win when they should lose on the merits.”

At the start of the hearing, Giuliani appeared before an American flag backdrop, which he said he uses for a program he conducts over the internet, but the judge told him to change it to a plain background. He also at one point held up his grandfather’s heirloom pocket watch and said he was ready to relinquish.

Giuliani conceded that he sometimes did not turn over everything requested in the case because he believed what was being sought was overly broad, inappropriate or even a “trap” set by lawyers for the plaintiffs.

He also said he sometimes had trouble turning over information regarding his assets because of numerous criminal and civil court cases requiring him to produce factual information.

Liman labeled one of Giuliani’s claims “preposterous” and said that being suspicious of the intent of lawyers for the election workers was “not an excuse for violating court orders.”

Giuliani, 80, said the demands made it “impossible to function in an official way” about 30% to 40% of the time.

After the ruling, the former mayor issued a statement through his publicist saying it was “tragic to watch as our justice system has been turned into a total mockery, where we have charades instead of actual hearings and trials.”

The election workers’ lawyers say Giuliani has displayed a “consistent pattern of willful defiance” of Liman’s October order to give up assets after he was found liable in 2023 for defaming their clients by falsely accusing them of tampering with ballots during the 2020 presidential election.

A military appeals court has ruled against Defense Secretary Lloyd Austin’s effort to throw out the plea deals reached for Khalid Sheikh Mohammed and two other defendants in the 9/11 attacks, a U.S. official said.

The decision puts back on track the agreements that would have the three men plead guilty to one of the deadliest attacks on the United States in exchange for being spared the possibility of the death penalty. The attacks by al-Qaida killed nearly 3,000 people on Sept. 11, 2001, and helped spur U.S. invasions of Afghanistan and Iraq in what the George W. Bush administration called its war on terror.

The military appeals court released its ruling Monday night, according to the U.S. official, who was not authorized to discuss the matter publicly and spoke on condition of anonymity.

Military prosecutors and defense attorneys for Mohammed, the accused mastermind of the attacks, and two co-defendants reached the plea agreements after two years of government-approved negotiations. The deals were announced late last summer.

Supporters of the plea agreements see them as a way of resolving the legally troubled case against the men at the U.S. military commission at Guantanamo Bay naval base in Cuba. Pretrial hearings for Mohammed, Walid bin Attash and Mustafa al-Hawsawi have been underway for more than a decade.

Much of the focus of pretrial arguments has been on how torture of the men while in CIA custody in the first years after their detention may taint the overall evidence in the case.

Within days of news of the plea deal this summer, Austin issued a brief order saying he was nullifying them.

He cited the gravity of the 9/11 attacks in saying that as defense secretary, he should decide on any plea agreements that would spare the defendants the possibility of execution.

Defense lawyers said Austin had no legal authority to reject a decision already approved by the Guantanamo court’s top authority and said the move amounted to unlawful interference in the case.

The military judge hearing the 9/11 case, Air Force Col. Matthew McCall, had agreed that Austin lacked standing to throw out the plea bargains after they were underway. That had set up the Defense Department’s appeal to the military appeals court.

Austin now has the option of taking his effort to throw out the plea deals to the U.S. Court of Appeals for the District of Columbia Circuit. The Pentagon did not immediately respond to a request for comment.

Separately, the Pentagon said it had repatriated one of the longest-held detainees at the Guantanamo military prison, a Tunisian man who U.S. authorities approved for transfer more than a decade ago.

Ridah bin Saleh al-Yazidi’s return to Tunisia leaves 26 men at Guantanamo. That’s down from a peak population of about 700 Muslim men detained abroad and brought to the prison in the years after the Sept. 11 attacks.

Al-Yazidi’s repatriation leaves 14 men awaiting transfer to other countries after U.S. authorities waived any prosecution and cleared them as security risks.

The Biden administration, pressed by rights groups to free remaining Guantanamo detainees held without charge, transferred out three other men this month. The U.S. says it is searching for suitable and stable countries willing to receive the remaining 14.

In a statement, the U.S. military said it had worked with authorities in Tunisia for the “responsible transfer” of al-Yazidi. He had been a prisoner at Guantanamo since 2002, when the U.S. began sending Muslim detainees taken abroad there.

Al-Yazidi is the last of a dozen Tunisian men once held at Guantanamo.

Of those remaining at Guantanamo, seven — including Mohammed and his 9/11 co-defendants — face active cases. Two others of the 26 total have been convicted and sentenced by the military commission.