VirtualBox and Windows Vista

Now that I’d successfully virtualised Windows XP, it was time to turn my attention to virtualising a legacy Windows Vista system that I owned. My Vista inventory included:

  1. A custom-built desktop with a Pentium 4 processor running Vista Home Premium.
  2. A Vista Home Premium upgrade CD.

I found the experience of virtualising my copy of Vista more challenging that virtualising XP. Major highlights follow.

Licence considerations

Having a retail copy of a Windows Vista Upgrade DVD, the first hurdle to overcome, and probably the most important hurdle,  was to check whether the Vista licence could be transferred to another machine. Turns out the answer was YES!!!

VirtualBox considerations

Using upgrade media, did this mean I had to install a supported OS such as XP first and then apply the upgrade? This appears to raise all sorts of problems for VirtualBox. Once a guest OS is specified, VirtualBox doesn’t seem to handle upgrading to another guest OS particularly well.

For instance, the VM containers for XP and Vista are quite different in their makeup under VirtualBox in areas such as allocated RAM and disk space, hyperthreading capability, IDE vs SATA considerations, and the list goes on. Some quite creative solutions have been presented such as taking an image backup of virtualised XP using Clonezilla and then restoring that into a VM container set up for Vista. Nice, but hard work.

The solution is to use the trick described here. It allows Vista to be installed in a VM container designed for Vista. The trick relies on Vista being installed twice; the first time as a full install and the second as an upgrade. This will allow the Vista Upgrade Product Key to work.

Windows Updates

After the initial install of Vista, I manually applied SP1 and SP2 before allowing Windows Update to take over. SP1 has to be applied first as SP2 is not cumulative. After the application of SP2, there was still a large group of around 40 important patches plus other updates. A slow update issue will arise after this. The fix is described in this post. Once resolved, there will be another large group of around 190 patches plus other updates.


Words that describe my experience in key areas in getting Windows Vista to a functional state:

  1. Installation – Wow! There’s some clever people out there! 
  2. Windows Update –  Patience.
  3. File services – Trivial.
  4. Print services – Trivial.


  1. Transfer Vista license onto my new computer
  2. How to Clean Install Windows Vista with Upgrade Media
  3. Updates not working, it has been searching for updates for hours
  4. Problem installing Service pack 1 for Windows Vista 32-bit from windows update

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