Setup Couldn't Start Properly - upgrading Server 2016 to Server 2019

Eyal Shahar 1 Reputation point

I have virtual machines I am upgrading from Server 2016 to Server 2019 DC.
Most of the upgrades went just fine but for two of them I get the message:

"Setup Couldn't Start Properly. Please reboot your PC and try running Windows 10 setup again".

Most of the VM's were upgraded from Server 2012R2 to Server 2016.
Some were already successfully upgraded to Server 2019 DC using a copy of the same installation media.

There are no leftover folders like Windows.old and such.
No hardware issues as the are all VM using the same hardware.

Windows Server
Windows Server
A family of Microsoft server operating systems that support enterprise-level management, data storage, applications, and communications.
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  1. Limitless Technology 39,201 Reputation points

    Hi EyalShahar,

    It's never recommended to in-place upgrade servers, even though it does work very often. I have successfully upgraded 2012R2 to 2016 and 2016 to 2019 many times. This error is caused because of corrupt Windows Installation files from the previous Window are still on your system and it’s conflicting with the update/upgrade process.

    Run Disk Cleanup and Error Checking

    1.Go to This PC or My PC and right click on the C: drive to select Properties.
    2.Now from the Properties window click on Disk Cleanup under capacity.
    3.It will take some time in order to calculate how much space Disk Cleanup will be able to free.
    4.Now click Clean up system files in the bottom under Description.
    5.In the next window that opens make sure to select everything under Files to delete and then click OK to run Disk Cleanup. Note: We are looking for “Previous Windows Installation(s)” and “Temporary Windows Installation files” if available, make sure they are checked.
    6.Let the Disk Cleanup complete and then again go the properties windows and select Tools tab.
    7.Next, click on Check under Error checking.
    8.Follow the on-screen instruction to finish error checking.
    9.Restart your PC to save changes. Again try to run setup and this may be able to Fix Setup couldn’t start properly error.

    Please try booting the server in safe mode as this may bypass the error and allow the operating system to boot. You can then attempt to fix the

    Boot your PC into Safe Mode

    1.Press Windows Key + R then type msconfig and hit Enter to open System Configuration.

    2.Switch to boot tab and check mark Safe Boot option.

    3.Click Apply followed by OK.

    4.Restart your PC and system will boot into Safe Mode automatically.

    5.Open File Explorer and click View > Options.

    6.Switch to the View tab and check mark “Show hidden files, folders, and drives.“

    7.Next, make sure to uncheck “Hide protect operating system files (Recommended).“

    8.Click Apply followed by OK.

    9.Navigate to Windows folder by pressing Windows Key + R then type C:\Windows and hit Enter.

    10.Locate the following folders and permanently delete them (Shift + Delete):

    $Windows.~BT (Windows Backup Files)
    $Windows.~WS (Windows Server Files)

    Note: You may not able to delete the above folders then simply rename them.

    11.Next, go back to the C: drive and make sure to delete the Windows.old folder.

    12.Next, if you have normally delete these folders then make sure to empty recycle bin.

    13.Again open System Configuration and uncheck Safe Boot option.

    14.Reboot your PC to save changes and again try to update/upgrade your Windows.

    15.Now download the Media Creation Tool once again and proceed with the installation process.

    Run Setup.exe directly

    1.Make sure to run the upgrade process, let is fail once.

    2.After that make sure you can view hidden files if not then repeat the previous step.

    3.Now navigate to the following folder: C:\ESD\setup.exe

    4.Double click on setup.exe to run and continue with the update/upgrade process without any problems. This seems to Fix Setup couldn’t start properly error.

    Run Startup/Automatic Repair

    1.Insert the Windows 10 bootable installation media and restart your PC.

    2.When prompted to Press any key to boot from CD or DVD, press any key to continue.

    3.Select your language preferences, and click Next. Click Repair your computer in the bottom-left.

    4.On choose an option screen, click Troubleshoot.

    5.On Troubleshoot screen, click Advanced option.

    6.On the Advanced options screen, click Automatic Repair or Startup Repair.

    7.Wait til the Windows Automatic/Startup Repairs complete.

    8.Restart and you have successfully Fix Setup couldn’t start properly error.

    I hope this answers your question.

    --If the reply is helpful, please Upvote and Accept as answer--

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  2. SG 0 Reputation points

    I had a similar issue when testing in place upgrades from 2012 to 2016 (the above suggestions did not help). In my case I found when logged in as "Administrator" into a restored VM for testing (network nic disconnected) I was getting the message:

    "Setup Couldn't Start Properly. Please reboot your PC and try running Windows 10 setup again".

    The fix was to log into the VM with the a domain account, and then the installation media ran correctly.

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  3. Richard Blunden 0 Reputation points

    Same issue here with 2012R2 servers to 2019.

    Got mine working if i added myself to GPO which allowed local rights to backup files and directories, manage auditing and security log and also debug programs. Worked fine after that. Same a settings needed if doing SQL security updates funnily enough which is what led me to the discovery. Great dialogue for that issue but totally rubbish for the Windows upgrades.

    Hope this helps.

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