I have the hard drive from a PC I used from 1999 to 2004 (I know, I should have upgraded from 98 by then), and I am trying to copy the whole user environment.

My attempts include:

Connecting HDD via EIDE/USB cable, using as disk for VMWare OS. Doesn't boot.

Tried to clone disk via 10.11 Disk Utility on Mac,

Set up working Windows 98 build on VM, and manually overwriting all non-system folders.

I know this is an unusual exercise that most people wouldn't put forth the effort to do, but I've been at it for a month every day now with different variations of the former.

How were users migrated in those days?

  • Just the user stuff, like documents and preferences? Or the whole system? – Ben N Dec 30 '15 at 3:09
  • I would like to copy the whole user environment, as it was. So when I log in, I want it to be exactly like it would be if I logged in again on the machine it came from. Like I want to log in and have AIM auto log in, winamp to start and have all the songs it had left off, same desktop items, window configurations, etc. I have read there are a lot of driver considerations which will affect whether or not I will have sound playback etc if I just clone the drive. – Electrik Dave Dec 30 '15 at 3:35
  • You could use VMWare vCenter Converter to turn your HDD into a VMWare virtual machine image that can then be run from VMWare Player; you could also create a blank VM with a VMDK the same size as the HDD and use a Live Linux distro to dd the physical drive to the VMDK ... after it's able to boot, you should be able to remove and reinstall any drivers as needed (probably all of them). – txtechhelp Dec 30 '15 at 7:18
  • Converter won't do Windows 98 – Electrik Dave Dec 30 '15 at 7:52

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