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“Clippy is still very annoying”: What happened when I switched from Windows 11 to Windows XP

Ivan Mehta by Ivan Mehta
February 7, 2026
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A man with a digital camera prepares to take a photo next to a billboard advertising the Microsoft Windows XP operating system.
(Image credit: Sean Gallup/Getty Images)

The world was very different 25 years ago. We ushered in the new millennium wearing low-rise jeans, looking THE Lord of the Ringsand listen to MP3s on iPods.

It was also a time when even the launch of a new operating system was as exciting as GTA6and with Windows XP, Microsoft abandoned its roots and created something aimed at everyone rather than just business users.

Monday: Installing XP

Screenshots of Windows XP running in 2026

(Image credit: Future / Microsoft)

Installing Windows XP directly on modern hardware is possible, but requires significant integration and patching. The easiest way to run Windows XP is to use a virtual machine. UTM is designed to do just that on macOS computers.

Screenshots of Windows XP running in 2026

(Image credit: Future / Microsoft)

Yes, I could have done this on a Windows device, but running it on a Mac increases security because if a virus or malware jumps from the virtual machine to the full operating system, it won’t be able to do much damage.

This is a good time to mention that if you want to run Windows XP in any way, it hasn’t been updated for over 10 years now, leaving it as vulnerable as a puppy in the center of the sun. So be careful.

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Screenshots of Windows XP running in 2026

(Image credit: Future / Microsoft)

The next step is to install a Windows XP ISO. I was hit with a rush of nostalgia remembering how exciting it was the first time I installed Windows XP, and I think Microsoft was fully aware that those first steps were meant to be a tempting appetizer, so it made everything as beautiful and easy as possible.

With Windows XP, Microsoft has truly created something different.

After entering the CD key (remember that!?), the installation takes a good half hour, then Windows XP announces its presence with that classic startup sound. This sunny wallpaper from Bliss appeared and something stirred deep within me.

Screenshots of Windows XP running in 2026

(Image credit: Future / Microsoft)

With Windows XP, Microsoft has truly created something different. It was nicknamed Fisher-Price OS for a reason: it was tactile, chunky, and colorful. As childish as it may sound, it was never boring.

Tuesday: Windows XP update

Screenshots of Windows XP running in 2026

(Image credit: Future / Microsoft)

One thing my rose-colored glasses had blocked was the number of updates you need to install to get Windows XP up and running. Fortunately, Legacy Updatea fan-made program, installs all necessary updates.

Screenshots of Windows XP running in 2026

(Image credit: Future / Microsoft)

It perfectly replicates the Windows update process, presenting updates in Internet Explorer (the first time Microsoft has made things this simple) and taking hours. Once XP was updated, Microsoft realized that my copy had not passed real Windows validation. Goodbye, Bliss. Hello, dark wallpaper, my old friend.

Wednesday: How did we live without research?

Screenshots of Windows XP running in 2026

(Image credit: Future / Microsoft)

With Windows updated, I poked around in XP. It’s terribly slow, and I don’t know if that’s just the way it is, or if it’s because I’m emulating one OS on a completely different OS.

But one of the biggest realizations I had about Windows XP is that search really wasn’t part of the structure of the operating system in 2001. Today, it’s second nature to press the Windows key and type the first few letters of the program or file you want to open.

Screenshots of Windows XP running in 2026

(Image credit: Future / Microsoft)

In Windows XP, opening files is done entirely with the mouse and you need to know what you’re looking for. I’m pretty sure Microsoft put more effort into the little animated dog than into the search itself. It’s such a minor thing, but it brought home how essential search is for an operating system’s user interface to be completely seamless.

Thursday: Productivity

Screenshots of Windows XP running in 2026

(Image credit: Future / Microsoft)

After a good old five o’clock Pinball session, I decided to try to do something, and it requires internet. Windows XP comes pre-packaged with Internet Explorer 6, and yes, it still sucks, but only because it’s so old and so fragile that almost every modern website makes it crash instantly.

Screenshots of Windows XP running in 2026

(Image credit: Future / Microsoft)

There are exceptions: FrogFind is a lo-fi search engine designed specifically for older computers that reduces code and images from modern sites to raw HTML. If you have a fetish for royal blue Times New Roman text, you’re in for a great time.

Either Microsoft’s Windows XP crash servers are still working 25 years later, or it was all a big lie.

The alternative is Additionalwhich, on paper, is a truly impressive feat. Designed specifically for retro computing, Supermium brings a Chromium experience to outdated operating systems. When it works. In my case it didn’t and I couldn’t even enter my Google username without it crashing.

Oddly, Windows XP still insisted on sending a crash report to Microsoft. Either Microsoft’s Windows XP crash servers are still working 25 years later, or it was all a big lie.

Screenshots of Windows XP running in 2026

(Image credit: Future / Microsoft)

The Internet wasn’t going to see the light of day, so I went the Microsoft Office route for work instead. After an hour of installation, Office refused to accept my product key for no apparent reason and kept restarting itself. Clippy was still present. Clippy is still very annoying.

Friday: Entertainment

Screenshots of Windows XP running in 2026

(Image credit: Future / Microsoft)

With any hope of finishing the job out the window (ahem), I decided to relax for some fun. Internet streaming is a total failure. YouTube tried to load, but didn’t get past the gray thumbnails.

Fortunately, Winamp still exists and, in keeping with the times, I raided my collection of an MP3 from 2001 for a blast of nostalgic tunes, just stared at these cool visualizations for about five minutes and remembered that this was all we had before Netflix.

Screenshots of Windows XP running in 2026

(Image credit: Future / Microsoft)

I also managed to get Half-life to run in 640 x 480 software mode, but I got stuck on the train and could only look at the ceiling. This is also something that has happened to me a lot in real life.

In conclusion

I pressed Shutdown one last time and vowed to never go back to Windows XP. It was a nostalgic trip that quickly turned into a nightmare.

I could I persevered, but I put too much emphasis on my mental health. Windows XP is slow, clunky, and just plain annoying in ways I’d completely forgotten about. I ran into Windows 11’s loving arms and welcomed its penetrating, AI-powered fingers.


An Apple MacBook Air on a white background

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