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Some notes on my Windows 10 upgrade processes

Posted by jpluimers on 2016/12/26

Shortly before the “Free Windows 10 Update” deadline I upgraded a bunch of physical and virtual machines each with different configurations providing various challenges.

Back then, I didn’t have time to properly write down notes so I saved a bunch of links. Now I found time to add a few notes below.

Windows Editions

Note there are fewer Windows 10 editions (Home/Pro/Enterprise) are different than before so there is a mapping (for instance Windows Ultimate does not map to Windows Enterprise): Windows 10 free upgrade matrix.

Getting the Windows 10 ISO image

It’s much easier, faster and disk-space friendly to install from ISO than waiting for GWX.exe or GWXUI.exe, especially when installing multiple systems in a row.

I don’t use x86 systems any more so I used Win10_1511_2_English_x64.iso which is slightly newer than Win10_1511_1_English_x64.iso and is likely to be outdated by now so get yours through

If you insist, there is Win10_1511_2_English_x32.iso (note the x64 -> x32 consistency, many people refer to it as x86 though).

Mounting ISO images

Windows 10 does not like to upgrade when you have the Daemon Tools ISO mounting tool installed. But Portable WinCDEmu is fine.

The Windows 10 installer doesn’t suffer from Portable WinCDEmu not mounting after reboot: during the first install step it copies enough to continue without the ISO image mounted after reboot.

Installing using (Virtual) CD drive

Just run the SETUP.EXE in the root of the CD drive.

Creating bootable media

Some systems do not have optical media any more so you need to create bootable media.

In the past, you used ImageX for that (e.g. Step-by-Step: Basic Windows 7 Deployment for IT Professionals), but as of Windows 8/Server 2008 R2 there is DISM: Apply Images Using DISM.

I used this command-line to copy from H: (the content of the ISO image) to V: (the VHD drive):

dism /apply-image /imagefile:H:\Sources\install.wim /index:1 /ApplyDir:V:\

More information at DISM Image Management Command-Line Options and DISM.exe Replaces ImageX.exe – My Thoughts On IT… (you can even use it to backup/restore file-based Windows images).

Multi-boot / boot configuration data

In the past (think Windows XP and earlier), you had BOOT.INI to choose which one to boot. Now there are msconfig and Boot Configuration Data editors like bcdedit and bcdboot for that:

Installing on VHD

You cannot update Windows 10 on a “Boot to VHD” based system: it’s one of the limitations in What is not supported for native boot when using VHDs:

  • Upgrading the operating system booted from a VHD. If you boot from a VHD, you cannot upgrade the Windows version in the VHD to a newer version.

There is a cumbersome workaround using Hyper-V which I didn’t use (look for “How do I install the November Update if Windows 10 is running on a VHD using native boot?” in Hands-on with Windows 10: Upgrading, installing and activating in the real world | ZDNet).

These are the steps I used to get it on a VHD (based on the How to install Windows 10 to VHD and create a dual boot system with Win 7/8 video below):

  1. Download the ISO
  2. Mount the ISO
  3. Create a VHD using Disk Management (diskmgmt.msc)
    1. Ensure 20 gigabytes or larger (I used a pre-allocated disk)
    2. Name it appropriately (note the name)
    3. Initialise it using MBR
    4. Create a new “Simple Volume” formatted as NTFS
    5. Mount it (I used V: drive)
  4. Start a command prompt (cmd.exe) as Administrator and confirm the UAC prompt
    1. Image the ISO to the VHD using DISM (see command-line above)
    2. Add the VHD (drive V:) to the boot list: bcdboot V:\Windows
  5. Using MSCONFIG ensure the Windows 10 VHD boots as default (it will reboot at least once during installation)
  6. Complete the Windows 10 Installation
    1. Enter the key used for the original Windows system or a new Windows 10 ke
  7. Optionally Using MSCONFIG ensure the original Windows 10 VHD boots as default (it will reboot at least once during installation)

You can use an existing VHD for DISM in which case you might need to Resize/extend virtual hard disk to get more space under Windows 7/8/10.


Key validation issues

If you get an error 0x80041023 during key validation at install time, then retry it later. Often the validation then just works. If it doesn’t, try to Activate Your Windows 10 License via Microsoft Chat Support or phone based activation:

  1. Press Windows key + X then clickRun, then type: slui.exe 4
  2. Next press the ‘ENTER’ key
  3. Select your ‘Country’ from the list.
  4. Choose the ‘Phone Activation’ option.
  5. Stay on the phone (do not select/press any options) and wait for a person to help you with activation.
  6. Explain your problem clearly to the support person.


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