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.

Leave a Reply

Your email address will not be published. Required fields are marked *

This site uses Akismet to reduce spam. Learn how your comment data is processed.