Running Windows 98 on an Apple Silicon Mac: A practical guide and some thoughts

If you're curious about old Windows versions and want to try them out on a modern Mac with Apple Silicon, it's actually fairly easy to do. After a discussion with my wife, we were curious to go back to some old nostalgic applications and games, so I looked into setting them up and figuring out what has changed... and what hasn't.

Let's get started!

Windows 98 uses a different processor architecture compared to modern Macs, so we'll need to use software to emulate an older environment. There are both paid and free options available. From my testing, nothing is perfect as there are no more commercial use-cases for running these older operating systems. Nevertheless, there are communities still working on improving compatibility to this day.

I ended up using the UTM application, which is powerful yet minimalist. Note that at the time of this writing, the QEMU version (the emulator used by UTM) in the stable release has a bug that prevents the installation of Windows 98. To bypass this bug, use the 4.6.0 beta release.

Installing Windows 98 is fairly simple. First, get yourself the ISO from the Internet Archive or Google. Then, configure the VM and proceed with the installation. If in doubt, I would suggest checking out Jens Depuydt's fantastic article. He even provides a file with some additional drivers that you might find useful, especially for network connectivity and graphics.

If you're struggling, here's a reference to the QEMU arguments that are used by UTM under the hood. I would love to share a download link to the VM, but considering everything is still technically copyrighted, I'm not sure that would be very wise (but feel free to send me a message).

Technically, the copyrights of programs published in the nineties won't expire for many more decades. But thankfully, nobody seems to be fighting to remove those ISOs from the web. Ideally, copyright wouldn't apply for so long or would be lost once the holder stops using it (as is currently the case with trademarks), but this is better than nothing.

The Internet Archive is a fantastic repository of all the programs you could want to install (Office 97 Professional Edition, SimCity 3000, Encarta, RollerCoaster Tycoon, etc.). Just find what you need and download the ISO. 

Overall, installing and running those applications works surprisingly well. The only exception for me are some games that rely on DirectX. I can't get them all to work as expected.

After playing a bit with all those apps, I was both surprised by all that's changed and at the same time stayed the same.

Games are by far the hardest to recognize. Graphically, as you would expect, they are unrecognizable. But what makes them challenging to play is the gameplay. Over more than two decades, game designers have vastly improved the ways we interact with elements in a game. This includes interacting with NPCs, navigating around the map, managing your inventory, etc. Everything used to be harder and more tedious. Games also used to be a lot more difficult, leading to bigger payoffs when they were finally defeated, which is a big part of why we remember them so fondly today.

Out of curiosity, I also played around with Office 97 Professional Edition and was surprised by how little has changed. Word and Excel are basically the same, and most people wouldn't miss any features from the latest version. Since 97, it's mainly the internet that has changed those applications by making collaboration and sharing a lot easier.

But what has mainly changed is outside of those applications: Around the start of the millennium, SaaS applications began their growth and gradually enabled workflows and automation that those apps just couldn't achieve for most users.

By contrast, this also means that in 98, if you were a power user of the Office suite knowledgeable in VBA, you could easily 10x the productivity of others. You could already connect applications together, create pseudo-apps in Excel, connect computers together, etc. That must have been incredible to those just getting started with their first computer. This, of course, was highly challenging as most of your knowledge would have had to come from books!

This was a fun little exploration. If you have a couple of hours, I highly recommend giving it a try.