There’s quite a few OEM customizations included here, so I’m curious what gets transferred over and if anything breaks. The original system came with Windows ME which was built on the 9x/Hybrid DOS kernel.
Windows XP

Since we are going from a 9x to NT-based install, changes are going to be drastic with new device drivers requiring to be installed. Before installing, Windows does a compatibility check for existing applications and drivers and will alert if any are found to have issues or require updates. This only alerts if Windows finds a known issue with the program based on Microsoft’s testing, some lesser-known applications might not have been tested.

The install appears to have started, but after a few seconds the screen went blank and the VM was unresponsive. Rebooted and was greeted with an option to start Windows or cancel XP Setup.
Booting into Windows ME instead boots directly into the XP Setup, which appears a little darker than usual

Not sure why it’s prompting to create a password, never seen that before

The default desktop post-upgrade, along with the eWare banner above the taskbar

Adaptec CreateCD requires an upgrade before it can function. Interestingly is this is generated by Windows XP. RealJukebox works but failed to load the previous files since the documents directly have changed from Windows ME. What’s strange is the music files have been renamed?
Windows Vista

And we hit the wall, since the drive is formatted as FAT32 from the ME install, we cannot install Vista without reformatting the hard disk. We also have to convert FAT32 to NTFS

There were a few obstacles, first we had to expand the VMWare disk, as it was set to 8GB by default. Once expanded we had to extend the partition which wasn’t possible in XP’s disk management utility, so I had to use an old version of EASEUS Partition manager to extend the partition.
We can also use EASEUS to convert the disk to NTFS, so we can finally install Vista, and hopefully Windows 7. Before conversion, a quick disk check is done.

Some issues were found but some of these are part of the VM and might not apply to the actual machine, either way it lets us continue

The Flyswat toolbar appears to be broken, and we are missing some buttons on the eWare taskbar

Some of the Windows 98 themes still remain and surprisingly they work. Color schemes, sounds and screensavers.

Adaptec CreateCD has now stopped working completely and will not launch, instead displaying the above dialog box. Later versions of Windows usually keep a database of incompatible programs, including ones that require patches to work.
Windows 7
Install was a lot easier since most of the prep work was done for Vista

Application compatibility is the same as Windows Vista, Meanwhile the icons on the eWare toolbar have started to function gain. It’s rare that you will be able to install this on the actual machines without extensive upgrades, and I’d imagine the eWare links would also long be dead at this point. Also the eWare toolbar sticks out like a sore thumb when combined with the Windows 7 taskbar.



























