Back at the turn of the 21st century, computers were still developing into what they'd become today. As such, we saw some really weird decisions made by hobbyists and companies that would shape how things would evolve over the years. For instance, there was TempleOS, an entire operating system designed by a man inspired by God.

Today, we're going to be taking a deep dive into the world of Lindows, and, for reasons you've probably already garnered from its name, the struggles it had with a young Microsoft back in the day.

Lindows wanted to fix a common Linux problem in the wildest way possible

And it tried to achieve it really early on in the tech scene

If you've ever moved from Windows to Linux, you'll know that you can't take every app with you. While some of your programs will have a Linux-native variant, others will require a workaround, others require running it through Wine, and others still won't work no matter what you do. But what if this problem was solved long, long before modern-day Windows? What if, say, we got over that hurdle all the way back in 2001?

Well, that was the goal of Lindows OS. As you might imagine from the name, Lindows is a portmanteau of Linux and Windows. The premise was simple on paper, but wild in practice: ship a Debian build of Linux and push everything that wasn't native through Wine. That way, people can use Linux without giving up their Windows apps.

Now, remember, this feat is pretty tricky to do today, in 2026. There are still apps that don't work properly in Wine; for instance, at the time of writing, there's a big fight to get Photoshop working properly through it. Now rewind our tech a quarter of a century and try it there.

The thing is, Lindows wasn't just a fun hobby OS. Its creator, Michael Robertson, wanted to have pre-built PCs shipped with Lindows on them. And he managed it, too; Walmart used to sell Lindows-based computers off the shelf until 2004.

Unfortunately, by the time the PCs hit the market, the Lindows team had discovered that solving the compatibility problem by squashing apps through Wine and calling it a day wasn't working as well as it had hoped. It instead pivoted to focusing on its Click-N-Run (CNR) subscription service, which let you install Linux apps with a single click.

Microsoft takes Lindows to court

And threatens its own Windows trademark in the process

As you might imagine, Microsoft wasn't stoked about the presence of Lindows. It was very protective of its Windows trademark, so it took Lindows to court in the US. Its main argument was that Lindows was deliberately named to confuse people between it and Windows, and that Microsoft should have control over the term "Windows."

However, the Lindows team counter-attacked with an ingenious argument. They said that, long before Windows got its name, the tech world was calling the GUI element a 'window.' Windows was named after the concept of the window, and as such, Microsoft had no business throwing its weight around with the Windows trademark, as it was a generic term rather than something that represented a company product.

The judge overseeing the US case, John Coughenour, was swayed by this argument and denied Microsoft's request to block Lindows from using its name in the United States. Microsoft had better results in European courts, but if it didn't act quickly, it would risk watching its household name reduced to an uncopyrightable generic term.

Microsoft ends the feud by purchasing the Lindows name

If you can't beat them, offer them a lot of money

Faced with an ongoing trial and the very real risk of losing the Windows trademark, Microsoft decided to end the court case at the cost of a lot of money. It offered the owners of Lindows $20 million in exchange for both the Lindows brand and its website domain name. Lindows as a company would still exist independent of Microsoft, but it could no longer use the term 'Lindows'. The Lindows team accepted.

Now the Lindows team had a lot of money, but they had to get off the word 'Lindows' by September 2004. Its answer was to rebrand to Linspire, and it's still going today. It's no longer the Wine-focused OS it used to be, instead pivoting to become a distro you can purchase for $41. Microsoft, now owning the very trademark that threatened its own, continued naming its OS Windows, and seemingly never used the term 'Lindows' for anything. Microsoft likely purchased the rights to the Lindows name specifically so it could bury it forevermore, and given how not many people even know Lindows existed, I'd argue that it succeeded.

Microsoft paid $20 million for a single letter

If you ever feel bad about a big purchase, just remember that, back in 2004, Microsoft shelled out a lot of money to ensure it had access to its own brand name with a single letter swapped in it. It's cool to think about what would have happened if Microsoft stuck to its guns and lost; there's a very good chance we wouldn't have Windows or a Microsoft-based OS at all.