Windows 8 upgrade problems? Join the club

By | August 25, 2012

Turns out I wasn’t the only one having problems upgrading from Windows 7 to Windows 8 after the RTM went live for the lucky TechNet and MSDN subscribers.

Unfortunately, Microsoft doesn’t consider us worthy of support just yet – probably because we are self-proclaimed expertsSmile

At any rate, I couldn’t give up on my upgrade.

“Dude, why not just do a clean install?” you ask. Excellent suggestion, however I’m one of the unfortunate few to not have multiple computers at home, specifically one that I can play doctor on. So, in my house, there’s one computer and everybody uses it. That includes my wife – a budding professional photographer – who has invested quite a bit of time and money in to software, templates, add-ons, and other things that make her job easier, faster, and unique. What this means for me, relative to the topic at hand, is “if you lose any of my shit, I will be severely pissed.” – so yeah. Upgrade was the only option. (who wants to reboot a PC every time they sit down? dual boot just wasn’t going to cut it either)

So, in true “this computer will not defeat me” developer fashion, I started on my 4th upgrade. And that’s right, this time it worked. So, since I posted on a couple of community & support forums for help with this and got nothing, I feel it is my duty – since I finally have an outlet in this blog – to unlock the secret to a successful Windows 7 x64 Ultimate to Windows 8 x64 Pro RTM upgrade, at least in my situation.

TL;DR: Uninstall IIS7 from your Windows 7 installation before upgrading to Windows 8

My process – Failure

  • Begin installation from within Windows 7 (the only way to do an in-place upgrade) by running setup.exe from my USB drive created from the Windows 8 ISO using the Windows 7 USB/DVD Tool
  • The purple “Preparing” screen would run to completion within Windows 7, and then the computer would reboot
  • Upon reboot, the Windows 8 logo would appear, and “Getting Devices Ready _%” would show on the screen w/ a progress indicator. The monitor would flash (presumably getting video drivers migrated), then the computer would reboot again
  • This time, the Windows 8 logo would appear, then “Getting Ready” would show w/ a progress indicator. After some time of just the logo & this text, a Windows-classic-themed dialog box would pop on the screen:
  • After clicking ‘OK’ the entire installation would roll back and I’d be back to Windows 7 just as if nothing happened. While frustrating and disappointing, this was pretty impressive I have to admit. It was literally just as if I’d never attempted the install at all.

I went thru my PC and uninstalled any software I don’t use anymore, paying special attention to “heavy” things like SQL Server 2008, SQL Server 2012, Visual Studio 2008, etc. I tried to think like Redmond and a “happy path” upgrade – the average consumer isn’t going to have Servers running on their Windows 7 install.

I tried the upgrade again, it failed just the same. I posted on some forums to see if I could find a log file. I got no answer, and went spelunking on my own. Lo and behold I found some magic at
and in that log file I found the faintest hint of a clue as to what might cause it, with “error” popping up pretty consistently related to IIS components.

The keystone

Then I remembered that Windows 8 has an upgraded version of IIS. I had IIS enabled in Windows 7 to do testing and debugging on web services I’ve written for my Windows Phone applications. I bit the bullet and uninstalled IIS from Windows 7. I then fired off the Windows 8 upgrade once again and the angels smiled upon me. It worked!

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  • John

    Very interesting write up but where do I find IIS.on my system?

    • Brandon

      Go to Programs and Features, Add/Remove Windows Features – it’s in that list.

  • JD

    Thanks for the article! I encountered this same issue when upgrading Server 2012 to Server 2012 R2. Removing IIS did the trick. Cheers!

    • Brandon

      Awesome, glad to hear it!

  • Brian Gochnauer

    For those that may not quite be in the same position and want a clean install quickly
    You can use USMT hardlink by;

    *MOVE* files to windows.old directory and install the new OS then run USMT scanstate (backup) and loadstate (restore) with hardlink option

    Boot a windows pe disk

    md c:windows.old
    move c:users c:windows.oldusers
    move “c:program files” “c:windows.oldProgram files”
    move “c:program files (x86)” “c:windows.oldProgram files (x86)”

    move c:windows c:windows.oldwindows

    Then run the windows install
    THen run USMT loadstate and scanstate with hardlink option

    I’m sure there are more complete descriptions out there; but this is the idea behind them