Installing Windows 98 on Virtualbox on MacOS

My attempt to install Windows 95 on Virtualbox on my Mac Pro didn’t turn out too well as by the time the installation completed it refused to boot with the error:

"While initializing device IOS. Windows Protection Error"

What on earth Windows 98 was doing back then initializing iOS devices is interesting, but beside the point 🙂 This error is described in this KB article but I’m not sure updating the BIOS in my Quantum hard disk is really applicable in this case. More likely the issue is related to VT-x virtualization  (I can’t find the option to turn off VT-x support on my VirtualBox install), or other posts suggest this is most likely to do with host CPUs faster than 2.1GHz, and my Mac Pro has dual 2.8 Xeons.

Moving on then, next up, installing Windows 98. There’s a great post here that describes VM specific settings compatible for installing 98 – I went with 1GB RAM and a virtual 10GB disk and followed the other suggested settings.

I booted the VM from a floppy disk image (the same I downloaded for my 95 installation attempt, from here), partitioned and formatted the virtual disk, and then ran ‘setup’ from the CD:

Welcome to Windows 98 Setup: “the software that makes your computer more powerful, reliable, manageable, and entertaining”.

I’m glad 98 made my computer “more entertaining”.


“Sit back and relax” …





“Windows 98 supports new, cutting edge technologies” …





I remember using this ‘active desktop’ feature in 98, where you could have web content pinned to your desktop. An interesting IE feature that was discontinued from Vista onwards.





























It’s alive! Welcome to Windows 98. Given that VirtualBox does not have any supported/provided Guest Additions for WIndows 98 (or 95 for that matter), running under VirtualBox is incredibly slow and sluggish. However for nostalgia’s sake, if there’s something you want to play around with to re-live just how awesome Windows 98 was (?), then it’s definitely doable in VirtualBox, but not a great experience.

Installing Windows 95 on VirtualBox on MacOS

Looking through a stack of CDs and DVDs on the shelf on my desk, amongst many other things I still have install CDs for Windows 95 and Windows 98. I wondered (as you do, well, maybe not everyone does) what it would be like to install 95 again from scratch so created a new VM in VirtualBox and off I went. If you’ve come across any of my posts before you might remember I’ve installed all sorts of OSes under VirtualBox before, because, well why not? OS/2 and AROS probably the most interesting.

The steps in this blog are very useful for a guide. Windows 95 install CDs were apparently not bootable, and I don’t remember having boot floppies. If I did I probably don’t have them anymore. I download a Windows 95 boot disk floppy .img from here, and attached it to the floppy drive in the VirtualBox config for this machine.

After booting to an a: prompt, attempted ‘format c:’ but got a ‘invalid drive specification’ error. Seems I needed to partition my blank attached virtual disk first, so from the a: prompt, ran fdisk:

entered ‘y’ for large disk support, and then selected option 1 for ‘Create a DOS partition’ and then ‘Create Primary DOS partition’. Next, formated it:

format c:

then change to R: (the attached CD Drive)

and then


Next, Windows 95 setup was telling me that my newly created and formatted disk was reporting an incorrect size, so started a Scandisk:

After this completed it still gave the same error, so I skipped this step:

Unfortunately at this point the install fails, and says the issue must be fixed before it will continue.

Possibly my 20GB attached virtual disk is not supported (too large), so reading around, it looks like a 2GB install disk is a supported size, so I was about to delete the 20GB disk and started again, but quitting the Scandisk before it completes with an error puts you back in the installer, and off it goes:

Some of the info screens during the install are rather interesting, promoting Window 95’s ‘high performance’:

“High-quality multimedia performance will dazzle you” – who wrote this stuff?

Who remembers dial-up MSN?

And then it fails ‘insufficient memory’ when booting up which is odd because I set the VM up with 1GB:

From post here and others, this seems this might be to do with having too much RAM configured for the VM, and in particular 1GB or more.

I decreased it to 512MB, then got:

This error on booting Windows 95 under VirtualBox seems related to VT-x virtualization. I can’t find the option to turn off VT-x support on my VirtualBox install, and other posts seem like this is to do with host CPUs faster than 2.1GHz, and my Mac Pro has dual 2.8 Xeons. Maybe this is as far as I’m going to get with 95. Next up, trying 98 :-0

Windows 95 launched 20 years ago today

On August 24th 1995 Windows 95 was launched. The minimum required specs were:

  • a 386 cpu (around 25MHz at the time?)
  • 4MB RAM
  • 55MB free disk space

Fast forward to 2015. The minimum specs for Windows 10 are:

  • a 1 GHz cpu
  • 1 GB RAM for 32-bit or 2 GB for 64-bit (really? I find this hard to believe, 4GB probably a realistic minimum, 8GB to be comfortable)
  • 16 GB disk space for 32-bit OS, 20 GB for 64-bit OS

Somehow this is supposed to be better, but I’m not sure exactly how. Running an OS in 4MB? How exactly was that possible?! That seems impossible by today’s standards. And yet, Windows 10 is so much better? Better at needing more resources than any previous Windows version?

If there’s one thing for sure, no-one has danced with such enthusiasm for the launch of a new operating system in the past 20 years since Steve Balmer, doing whatever he was doing here.

And yes, Windows 95, with your blue screens and all, “you made a grown man cry”.

I’ve always wondered what was the intent of using the Stones “Start Me Up” as the theme music for Windows 95. Yes ok, start button, “Start Me Up”, ok, I get it. But didn’t they listen to the rest of the lyrics? Maybe they were thinking crying in happiness, but in reality it was more often crying in despair :-0