In Supreme Court oral arguments over a potentially seismic change to the internet, the most memorable question came from Justice Samuel Alito. “One of the parties here is the owner of Pornhub, right?” Alito asked Derek Shaffer, lawyer for the adult industry group Free Speech Coalition. “Is it like the old Playboy magazine? You have essays there by the modern-day equivalent of Gore Vidal and William F. Buckley, Jr.?”

The massive adult web portal Pornhub, in case you’re wondering, does not publish essays by distinguished intellectuals. (Shaffer notes that it does host sexual wellness videos.) The question inspired a slew of commentary on social media, alongside a few quips directed at Justice Clarence Thomas, who declared during oral argument that “Playboy was about squiggly lines on cable TV.” But as funny as the quotes were, what the justices were getting at was hardly a joke: how much protection does sexual content and other legal speech deserve, if hosted online?

FSC v. Paxton concerns Texas’ HB 1181, which requires sites with a large proportion of sexually explicit content to verify users’ ages and post scientifically unproven health warnings about how porn “is proven to harm human brain development.” After a lower court blocked the law as unconstitutional, the Fifth Circuit Court of Appeals allowed it to take effect. Today, the two sides (as well as US Principal Deputy Solicitor General Brian Fletcher) argued mainly over whether that court used the correct level of scrutiny for evaluating the law’s risks. But the arguments also touched on larger questions — including whether the internet’s evolution makes old Supreme Court rulings obsolete.

“We’re standing at the crossroads of some pretty significant internet law right now,” says Christopher Terry, associate professor of media law at the University of Minnesota.

In some ways, it’s a very familiar crossroads. In the Reno v. ACLU and Ashcroft v. ACLU decisions between the late 1990s and early 2000s, the Supreme Court repeatedly found online age verification laws for adult content unconstitutional. On top of that, FSC v. Paxton is the latest in a recent string of internet law conundrums, including a case over banning TikTok — TikTok v. Garland — that was heard just last week.

“The level of sophistication and energy seemed a little lower at these arguments. I got a sense of fatigue from the justices about internet issues,” says Blake Reid, associate professor of law at the University of Colorado Boulder. “And I think that the age verification issue in particular is one that the court has confronted many times before.”

The current court has decided some past cases in narrow ways that don’t address larger questions about the internet. Reid thinks the justices appeared conflicted about whether to do that here — to, say, simply punt the case back to the appeals court. (The US government also appeared in court to promote a middle ground between FSC and Texas, opposing the Fifth Circuit’s ruling but not all age verification laws.) “They were trying to decide: do we resolve the level of scrutiny question, or do we get all the way to the answer of whether this is constitutional or not?” he says. “Can we make this not our problem in a very narrow way, or do we need to just dive in and deal with it?”

There’s one particularly glaring issue if the court does dive in. Those earlier rulings found that the age verification systems of the 1990s and 2000s unduly burdened people’s speech and that filtering software could serve the same purpose, but the court also said that if the internet changed at some point in the future, that analysis could change too. Justices, particularly conservative ones like Alito and Thomas, raised that possibility repeatedly today — asking how the porn landscape and age verification tech have changed, and by implication, whether Reno and Ashcroft could be irrelevant. “For the first time that I’m aware of, the court actually asked that exact question,” says Terry. “It asked it several times — whether or not these things are still good.”

Which brings us back to squiggly lines and Gore Vidal.

“It’s actually not that crazy of a question,” says Terry of Alito’s hypothetical, despite its oddly dated references. Texas argues that sites like Pornhub are obscene for minors, a standard that offers fewer legal protections and applies to works with no redeeming artistic or other social value, while the FSC argues that HB 1181 will catch things like sex education videos in its net. Thomas references cable TV, meanwhile, to claim “we’re in an entirely different world” of mass access to adult content today — creating a more urgent duty to keep it away from kids.

Gautam Hans, Cornell University law professor and First Amendment expert, says that overall no clear winner emerged today. “In terms of the range of outcomes, I think there’s a big range,” Hans tells The Verge. The end result depends significantly on how much the court decides to revisit its earlier decisions. “I think there was a feeling that technical filtering doesn’t work, or is insufficient, or we have more evidence that that’s actually not a good substitute in the intervening decades,” he says. This argument cuts both ways, though — because it’s not clear how well age verification would work either. “I agree that technical filtering is not a panacea. I don’t think that a panacea exists,” adds Hans.

Numerous states have passed age verification rules for online porn, and FSC v. Paxton could directly impact whether they stand up to legal challenges. But its impact could go beyond porn. Both TikTok v. Garland and this case deal with whether the government’s interests — national security for TikTok, protecting kids in FSC — should override free speech concerns. “We’ve got two major cases in five days dealing with whether or not traditional First Amendment law still applies to internet content in the same way,” Terry says.

And several state and federal lawmakers have demanded stronger age verification for social media, sometimes alongside a proposed ban on minors using it. Opening the door to porn verification wouldn’t guarantee those efforts would succeed, but Hans says it could make legislators far more likely to try. “I think that if the Supreme Court said that some form of age verification could be constitutional, that if you’re the state in other situations, they’re going to say, well, extend that reasoning to other substantive areas of internet regulation,” he says.

For now, Hans offers a gentle suggestion to the justices. “I think that Alito needs to get some more contemporary references,” he says.