Although Microsoft is making progress on making the installation process easier, there are still many upgrade issues, including cryptic error message like “Setup has failed to initialize the working directory” or “Setup couldn’t start properly”. Here are the solutions.

Error #1: Setup Has Failed To Initialize The Working Directory – Free Disk Space!

The first error message that you may encounter during the upgrade is this cryptic message: “Setup Has Failed To Initiliaze The Working Directory

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Basically what it tells you is that the Windows 10 installer was unable to create a working directory. Whenever that is the case, it’s most likely due to low disk space. So download our recommended tool to free disk space and locate all huge files and get rid of them!

Then start the installer again and you should be good to go!

Error #2: Setup Couldn’t Start Properly – Free Disk Space!

Now the second error message is even more cryptic for beginners: Setup Couldnt Start Properly

Setup couldn’t start properly? Why? It wouldn’t hurt to simply say, hey this computer is low on disk space, we can’t start the installer right now and you need to free some disk space first. It can’t be that difficult to do a simple disk space calculation before initiating the installer, right?

Anyway, simply free some disk space and the error will go away.

Error #3: You can’t keep Windows settings, personal files, and apps

The last error requires a little more effort. If the option to keep apps and files is greyed out, you need to make sure you created the correct upgrade disc. Unfortunately, the Windows 10 upgrade tool is not capable of upgrading an installation with a different default language (e.g. French, German, Polish, Spanish, Arabic and so on) to another language e.g. English or British English. What you need to do is look up the default language you chose when you first installed Windows.

I wrote a guide how to detect the default language when you’ve first installed Windows, you can read it here and you will then be able to keep apps and personal files and perform a full upgrade!

After you have upgraded your current Windows version, you can change the default language in Windows 10 quite easily. Read this guide if you need help with installing language packs.

Error #4: Windows 10 failed to install

If you keep getting the error “failed to install”, then check for Windows updates and hotfix. If your Windows update doesn’t work, run the following via an elevated command prompt:

wuauclt.exe /updatenow

This will force Windows to check for updates that could address the installation issues.

Other Errors?

Have you noticed any errors when you launch the Windows 10 installation tool (MediaCreationTool.exe)?

If so, we would really appreciate it if you could post the errors below so we can look into them and it surely would help others with similar problems to avoid those during the installation.