VirtualBox Windows 8 Upgrade from Windows XP

Windows Virtual Machines VirtualBox

This page has turned out to be the most popular on the site.  Which is a shame, because it’s WayOffScript for Bizzhacks, not the sort of stuff the site is for.  But I’ll leave it up as a public service:

I’ve just completed an upgrade from Windows XP to Windows 8 on my Oracle VirtualBox virtualization platform. It took me over a week to figure out how to do it, and I thought I’d post my tips here.  I’m currently a Mac user, but like many, I can’t quite seem to leave Windows behind.  I’ve been running Windows XP for many years, and have managed to skip the abhorent Windows Vista, and the quite good Windows 7, and gone straight for Windows 8, as I fear my upgrade path will disappear.  The whole experience has left me cold, but let’s go to that later!  So OS X Mountain Lion is my HOST system and Windows XP -> Windows 8 is my upgrading GUEST system.

Starting Up:  Since you’re on a virtual machine, you may as well clone your existing machine, and work with a clone, just to be on the safe site.  There’s a command from the menu that allows you to do this (Machine, Clone).  Another reason you’ll want to do this is that your applications will disappear in the upgrade progress – so althought it’s probably against the license terms, you may want to have both VMSs in the future!

Size Requirements: You need 16GBytes of drive available, so you might need to increase the size of your Virtual Machine.  To do this, you’ll probably need to use the command line interface for VirtualBox – so on Mac this would mean using Terminal.  The command to make it happen is:

VBoxManage modifyhd <path/to/vdi/or/vmdk> --resize <new-size-in-mbytes>

for example for a 35GByte disk:

VBoxManage modifyhd /users/adam/vm/my_vm/my_vm.vdi --resize 35840

Once that’s done, you also need your GUEST Windows to recognize it, as Windows will see it as two partitions.  I downloaded EaseUS Partition Master 9.1.1 onto my XP GUEST Windows to do this, and it has useful demo videos to guide you through the process of merging the partitions.

Now Change Your Settings:  This took me a while to figure out, and a couple of upgrade attempts got aborted.  You need to change the VirtualBox settings before you do the Windows Upgrade!  These are the settings you need, provided by JailBreakEye.Com (he’ s using an Windows HOST, but they’re the same for OSX – although the menu structure is a little different):





Do the Windows 8 Upgrade:  Now Do the Windows 8 Upgrade, using the Windows Upgrade Tool Provided by Microsoft; leave it for about 1 1/2 hours to do it’s thing, and it SHOULD work!

But are the results worth it?  Well it feels a lot like going back to Kindergarden!  And I’ll need to re-install most of the software I had, and I’m sure some won’t work.  My initial response is, no, it’s horrible, and Microsoft has completely lost the plot.  I hope I can eat my words on this one, but in the battle of the emerging “Intelligences” (Amazon, Apple, Samsung, Microsoft, Google, Facebook) Microsoft is starting to look like an also-ran.

Leave A Reply (9 comments so far)

  1. Chris
    7 years ago

    Thanks for sharing; I'm bookmarking for later use.

  2. Chris S.
    7 years ago

    This allowed me to upgrade from Windows XP to Windows 7 too. Thanks!

  3. Martha
    7 years ago

    Nice post

  4. Karl
    7 years ago

    Thanks mate, I've been trying to get this done all day!

  5. Jeff Clemons
    6 years ago

    Have similar experience EXCEPT it did not work! two attempts failed after using MS's tool to verify that VM was. so they said, comparable for upgrade to W8. not giving up yet just in research mode!

  6. Guest
    6 years ago

    Thank you very much for the info. I installed xp in virtualbox with 1024mb ram and a 25gb fixed hd, and 128mb of video ram. I mounted the upgrade iso, booted to xp, then autoran it. When it puked, I gogled my problem and found your solution. All I did though was power off the VM, and change my settings to yours. Then when I booted from the VM, I got a screen giving me the choices of booting Windows or going to setup. I chose setup and it installed and is working fine. I didn't have to download any of those utiities.

  7. Jonshos
    6 years ago

    I've already installed Windows 8 and looking forward to update with new version. I think upgrade version using is very possible way to be in touch with all latest benefits. But after reading your post I've come to know some delightful and precious knowledge about the Windows 8 and Windows Phone 8 from Microsoft. That is very handful to me.

  8. Motivational Quotes
    5 years ago

    Useful info. Lucky me I found your web site unintentionally, and I’m

    surprised why this twist of fate did not took place in advance!

    I bookmarked it.

  9. Victor
    5 years ago

    Useful tip, you save me from spending more time fixing MS Win8 update from XP. Thanks!

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