The legal system is often a confounding place, where disputes are adjudicated—it’s a world full of jargon that we journalists try to explain as best we can. And over the last two decades, legal cases have remained a fixture on Ars Technica.

We’ve brought you endless news of initial criminal or civil complaints in that time. And in the most important cases, Ars has followed them, blow by blow, through various motions. We sat in every session for the criminal trial of Silk Road mastermind Ross Ulbricht and took a similar approach to the API patents saga of Oracle v. Google, for instance.

Just this week, Ars sat in the courtroom as Defense Distributed and the State of New Jersey argued over legal jurisdiction and matters of free speech intersecting with future technology. It echoes back to our site’s legacy of watching the march of technology and innovation directly intersect with an evolving legal system—it has been nearly 20 years since we covered Microsoft’s infamous antitrust battles around the turn of the century. These literally became the subject of CNN decade documentaries since then.

So as Ars continues to reflect on the recent technological past as part of our 20th Anniversary, we wanted to look back at the most memorable legal cases of the site’s lifetime. To be clear, these are not necessarily the cases that have had the most lasting impact on the legal landscape—although many would qualify—but we think these cases stand out for their relevance today, the philosophical questions at hand, and often the memorable circumstances at a case’s core.

Reno v. American Civil Liberties Union

Filed: February 8, 1996
Highest court reached: Supreme Court of the United States
Decided: June 26, 1997
Result: Established that the Communications Decency Act’s provisions that attempted to criminalize the distribution of adult content online to minors were unconstitutional.

While this case is just barely outside of our 20-year timeline, multiple legal experts that we contacted insisted it be included on any list involving recent history.

Reno v. ACLU was the first time that the United States Supreme Court considered how the free speech provision of the First Amendment should apply to the Internet. And a unanimous court found that the law did not adequately define “indecent.”

Had the Supreme Court ruled the other way, it would have been punishable by up to two years in jail and/or a $250,000 fine for any Internet user to speak in an “indecent” or “patently offensive” manner that would be viewed by minors. Quite simply, the Internet as we know it would not exist (for good or for ill).

“We are persuaded that the CDA lacks the precision that the First Amendment requires when a statute regulates the content of speech,” Justice John Paul Stevens wrote for a unanimous court. “In order to deny minors access to potentially harmful speech, the CDA effectively suppresses a large amount of speech that adults have a constitutional right to receive and to address to one another. That burden on adult speech is unacceptable if less restrictive alternatives would be at least as effective in achieving the legitimate purpose that the statute was enacted to serve.”

Bernstein v. Department of Justice

Filed: February 21, 1995
Highest court reached: 9th US Circuit Court of Appeals
Decided: May 6, 1999
Result: Court ruled that computer code is speech and is protected by the Constitution.

This case was brought before Reno, but it took longer to be fully decided. In Bernstein v. DoJ, the 9th US Circuit Court of Appeals firmly established that computer code—like any other language—is protected by the First Amendment’s guaranteed right to freedom of speech.

Back in 1995, Daniel Bernstein, then a doctoral student at the University of California, Berkeley, wanted to be able to publish “Snuffle.” This program converted a one-way hash into a private-key encryption system.

Bernstein wanted to publish not only the algorithm involved but also a mathematical paper explaining it and the relevant source code. However, federal arms regulations forbade him from doing so. He and the EFF challenged this interpretation of the law on First Amendment grounds.

In 1999, the Ninth Circuit ruled along similar lines as the district court, and it took the time to discuss the relationship between encryption and privacy:

Whether we are surveilled by our government, by criminals, or by our neighbors, it is fair to say that never has our ability to shield our affairs from prying eyes been at such a low ebb. The availability and use of secure encryption may offer an opportunity to reclaim some portion of the privacy we have lost. Government efforts to control encryption thus may well implicate not only the First Amendment rights of cryptographers intent on pushing the boundaries of their science, but also the constitutional rights of each of us as potential recipients of encryption’s bounty.

The case obviously continues to have relevance today, as this week’s debate over the distribution of CAD files for printing firearms reminds us.

Kyllo v. United States

Filed: January 24, 1992
Highest court reached: Supreme Court
Decided: June 11, 2001
Result: The government’s use of an infrared scanner to peer inside someone’s home without a warrant is unconstitutional.

This case began on a tiny scale: a Bureau of Land Management agent thought that one 27-year-old man, Danny Kyllo, was growing marijuana inside his home. Why did the BLM believe this? Because an Oregon National Guardsman used a newfound device, a forward-looking infrared (FLIR), to scan the heat output from this modest home in Florence, along the Oregon coast.

In essence, the government claimed that the use of a FLIR was so small-scale and so non-invasive, it was more analogous to binoculars than a high-tech device. But five justices of the Supreme Court nine were unconvinced.

“Where, as here, the Government uses a device that is not in general public use, to explore details of a private home that would previously have been unknowable without physical intrusion, the surveillance is a Fourth Amendment ‘search,’ and is presumptively unreasonable without a warrant,” Justice Antonin Scalia wrote for the majority.

Given that newer versions of the FLIR that attach to the iPhone can be had for under $300, it’s not clear whether Justice Scalia’s “not in general public use” provision would still hold up in 2018. Still, Kyllo’s impact remains.

“The idea is that a search is a search, no matter what technology police use,” Andrew Crocker, an EFF lawyer, told Ars.