My Windows 10 Upgrade Experience

A brief overview of the steps I took to upgrade my Windows 8.1 installation to Windows 10.
created by on 2015-08-01

Windows 10 has been officially released on July 29th 2015 and since I am currently on vacation at home I took the time to upgrade my existing Windows 8.1 installation.


My Windows 10 upgrade experience in short:

Screenshot of my Windows 10 Desktop after the Upgrade with the Startmenu open


Forcing the Update

Even tough the GA was scheduled for the 29th this does not necessarily mean that’ll will get the upgrade right away. As it says in the mail you probably received after reserving the Windows 10 upgrade Microsoft will roll out Windows 10 in an organized way:

We want to give every customer a great upgrade experience, so we’re rolling it out in an organized way to manage high demand and to make sure that the upgrade is right for your device. After July 29, when Windows 10 is ready for your device, it will download in the background. You’ll then get a notification to schedule your upgrade right away or at another time that’s convenient for you.

Screenshot of the Windows 10 reservation confirmation mail

… which means that the upgrade was not available for me on the 30th of July. And it was still not available when I ran a normal Windows update:

Screenshot: Windows 10 Upgrade Notification Dialog

Screenshot: Windows 10 was not available via the normal Windows Update

Forced Windows Update

So I tried to force the Windows 10 installation using wuauclt.exe /updatenow from an admin console:

Screenshot: Forced Windows Update using wuauclt.exe /updatenow from an admin console

This seemed to work because Windows Update started downloading Windows 10 right away:

Screenshot: Windows Update downloading Windows 10 after a forced update

But after the download finished the installation failed. First there was a dialog which said the I should check my PC before the upgrade and that some updates failed:

Check your PC before upgrading
Before installing Windows 10 Insider Preview, something needs your attention.

Screenshot: Windows Update Error Message  - Check your PC before upgrading

And after hitting “Check your PC” I got an error indicating that some updates failed to install:

Some updates were not installed.
Failed: 2 updates

Windows Update Error after downloading Windows 10 updates: Some updates were not installed

I also tried clearing the C:\Windows\SoftwareDistribution\Download folder as it was recommended by some people:

Screenshot: Clearing the C:\Windows\SoftwareDistribution\Download folder

… but still no luck. So I tried a different method.

Windows Download Tool

Since the installation via Windows Update did not work I tried the Windows 10 Download Tool. You can just download it from and run it:

Screenshot: Using the Windows 10 Download Tool to install Windows 10

The tool will guide you through the download process and give you some upgrade “options”. Your “options” for upgrading are

So you chose “Only keep personal files”:

Screenshot: Using the Windows 10 Download Tool to install Windows 10

This is quite a bummer since I though it would be just an upgrade, but apparently Microsoft did not want to make any promises that they couldn’t keep afterwards. So you’ll have to reinstall all your programs after the upgrade to Windows 10.

Installation Process

Once the download was complete the installation process was straight forward without any issues.

These are the steps I took to download Windows 10 using the Windows 10 Download Tool:

Animation: Downloading Windows 10 uing the Windows 10 Download Tool

And these are the steps of the installation process:

Animation: Windows 10 Installation

If I think there were three reboots in total.


After you have successfully installed Windows 10 using the “Keep User Settings”-option you should cleanup your disk because the installer will move all files of the old system to C:\Windows.old. For me it was about 40 GB of data:

Screenshot: C:\Windows.old folder after Windows 10 Installation

You can manually delete the folder or use Windows’ Disk Cleanup utility:

Screenshot of the Disk Cleanup for C: after installing Windows 10

The Results

This is how my dual-screen desktop looks like after the upgrade:

Screeenshot of my dual-screen Windows 10 Desktop

If you want to learn more about the new features of Windows 10 you should check out Scott Hanselmann’s series: Getting Started with Windows 10.

Screenshot of Scott Hanselman Blog post about Getting Started with Windows 10

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