How to upgrade to Windows 10 under Parallels Desktop 10 for Mac

This article is for those of you who (like myself) are running Microsoft Windows as a virtual machine under Parallels Desktop 10 for Apple Mac OS and have experienced problems while attempting to upgrade to Windows 10 (from Windows 8.1 Pro in my case).

A couple of days ago Microsoft released Windows 10 and although the integrated update tool in Windows 8.1 Pro told me that “Windows 10 will not run on this PC” due to the Parallels display adapter (WDDM), I had been running a technical preview of Windows 10 in another virtual machine, so I was certain that my machine (Apple 13″ retina MacBook Pro, late 2013) would in fact be able to run it. I found a support page from Parallels which detailed a solution and felt ready to go. What followed was a frustrating mix of recurring (yes, I tried multiple times) “setup has failed to initialize the working directory” and “something happened” errors. Eventually, after realizing that doing the same thing over and over again probably wouldn’t change the outcome, I decided on a different approach which turned out to work flawlessly:

  1. Download the appropriate Windows 10 ISO file to Mac OS from
    1. Select the appropriate edition and click “confirm”. You’ll have multiple versions to choose from. Refer to this page for more info.
    2. Select the product language and click “confirm”.
    3. Download the Windows 10 ISO in either a 32-bit or 64-bit version.
  2. In Parallels 10 on Mac OS:
    1. Open the “(Parallels Desktop) Control Center” to view your virtual machines.
    2. Edit the virtual machine, that you wish to upgrade to Windows 10, by clicking the gear symbol/icon.
    3. Go to the “hardware” tab.
    4. Click “CD/DVD”.
    5. In the “connect to” select “choose an image file”.
    6. Locate the Windows 10 ISO file.
    7. Click “open.
    8. Start the virtual machine.
  3. In the virtual machine:
    1. Open Windows Explorer (hotkeys: cmd e).
    2. Click on the (“This PC” >) “DVD drive” to access the contents of the Windows 10 ISO file.
    3. In the list of folders/files on the ISO, double click the “setup” application.
    4. Complete the setup process and you will be running Windows 10.

That’s it. I hope it helps someone out there.

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