Don’t double-upgrade from XP to Windows 8.0 then to Windows 8.1

Since Windows Vista onwards – if you install windows on the same partition as an existing installation it will warn you and create a windows.old folder containing all your old installation files.
If you do this a second (or 3rd or fourth etc..) it just renames the existing windows.old to windows.old.001 or windows.old.002 etc.. and shuffles them along with no data loss.

I had the joyous time discovering that it is a bad idea to upgrade a computer from Windows XP to Windows 8.0 and then to Windows 8.1 in one swoop.

Windows XP cannot be directly upgraded to 8.0. You also can’t use the Easy Transfer Wizard to go from XP to 8.0 or higher.

You have to do a Custom install and select the partition. It helpfully informs you that the files from the old installation will be placed in “Windows.old”. I’ve done this many times and then once ready – copy all the required documents out of the “windows.old\Documents and Settings” folder onto the new setup.

I installed 8.0 and made sure that the files were indeed still in c:\windows.old – then decided that I’d copy the documents and photos after the upgrade to 8.1, there is little point spending time doing it when I might need to do more tweaks later.

I initiate the installation of the Windows 8.1 update via the App Store and it starts the download and then the installation without any user interaction, questions or prompts. It gets to the end and asks if I want to reboot. OK..

Reboot and it gives you the normal welcome prompts such as if you want Do not Track turned on etc.

I then get to the desktop and decide to copy the files from the old XP windows.old into my user folder.


But where the heck has my Documents and Settings folder gone?! In fact.. why is this a copy of the old windows 8.0 instalation?

It turns out that the Windows 8.1 installation just deletes the previous windows.old folder without warning or asking and replaces it with a copy of your 8.0 installation. It SHOULD rename the existing .old folder to .old.001 as Windows 7 did! (See screenshot at the top of this article).

Needless to say I was very, very angry. Pulled the power on the system asap and I’ve recovered the majority of the information using R-Studio. About 1 in 10 photos are corrupt and unreadable, I presume the same might be true when I go through some of the documents.


I’m pretty livid that the upgrade does this. I would understand if the upgrade were on CD and worked similar to the Windows 7 and 8 installation procedures but the App Store and “no touch” installation procedure makes you think it is literally just an in-place upgrade similar to the regular windows updates or app installations. There is no message or reason to believe that the windows.old folder would even be created – let alone a previous iteration being entirely wiped out!

I’m posting this in the hope that it stops someone else “getting got” by this issue. The golden rule is – I suppose – Backup! Then it isn’t a problem if one copy of files gets unexpectedly lost.

If you have fallen for this and you are wondering where your files are. Unplug the computer ASAP. Don’t use it. The more you use your computer the more chance that you won’t get stuff back. There is already a slim chance of recovery anyway and the longer you use it the less chance there is.

Then consult someone experienced in recovery of deleted files. They should remove the drive from the computer in questions and plug it into a different computer as a slave and then use software such as R-Studio to recover the files.

It also seems that Microsoft have introduced automated cleanup of the windows.old folder as of windows 8.1 or possibly windows 8 too.

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1 Response to Don’t double-upgrade from XP to Windows 8.0 then to Windows 8.1

  1. Shannon W. says:

    I had a hell of a time searching for this on Google (to see whether I was imagining it or not). Everything that came up was about how to delete the Windows.old.

    I’ve had it happen at least twice now.
    Customer brings in machine,
    fixing the Windows installation turns out to be unfeasible,
    perform a new Win8 install,
    be happy because all the docs and such are there in Windows.old,
    perform 8.1 update,
    There’s no Windows.old.001!!! AND my Windows.old was deleted!!!

    Same happens if you re-install Win7 or 8.1 and then upgrade to Win10. It deletes the existing Windows.old.


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