Migrating a win 98 machine to a VM?

Is there an easy way to copy an image of a windows 98 laptop into a disk image and then boot that in a VM?

My old man has a license for Autocad 2000 and wants to keep using it for newer projects. The stuff he uses it for is mostly for audio and electrical setups, and is not demanding enough for a current version. However, being a cheapskate runs in the family and he really wants to keep using the old version and not the subscription SaaS crap they're doing now. Until now, he's been using a 'vintage' dell machine to run it. Since support was pulled for 90SE he hasn't connected it to the internet or any networks, it's been 100% an offline CAD machine.

My plan, now that the Dell is starting to really rust, is to move the windows 98 image into a VM and boot it on my old thinkpad inside linux. This way I can get some great linux experience setting it up, and he can continue getting the most of 15 year old software. Now, I have only made machines inside Virtualbox and qemu, and even booting a real drive as a .VMDK with raw access. My plan so far is to stick it in my HDD dock and #dd if=/dev/sdx of=/path/to/image.file it onto an image file on the thinkpad, but after that I'm kind of lost. I know that win98 doesn't handle system changes very well, and I'm also not sure if that image will open as a VDI. I have used VirtualBox a lot and qemu a little, but feel overall fairly comfortable so far.

So, is this even possible? Are there significant modifications I would have to do to the installation to make it VM-able? Please drop me some advice and talk me out of this!


Not an easy thing to move, as Windows will detect the change in the underlying hardware. If you still have the original installation CD it might be possible to install it in virtualbox, but it probably wouldn't run very well even then.

You might find your CAD software will run on Windows XP, in virtualbox. You can test this by downloading a virtual version of XP, for virtualbox, from Microsoft.

Link: http://dev.modern.ie/tools/vms/

There are other versions of Windows on the same site too.

I do have a working 98SE machine in VB. I might try installing it in that machine if i can find some installation media.

Your link for the XP vms doesn't seem to work for me. the first drop down menu is empty. Is there a secret or is it classic Microsoft shittyness?

Thanks for the reply!

I made a Win 95 VM a while ago. While it boots like an 8 legged dog. No current browsers worked and the built in ones crashed on all the modern sites.

Fun, eh? My win95 vm only works like half the time at best. So just like real windows 95 PCs. Did get some free AOL hours though so that's nice.