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I am trying to install Windows Server 2019 Standard Edition in Virtual Machine Windows.

Devyani Jaiswal 0 Reputation points
2025-10-06T14:45:05.94+00:00

I am trying to do setup for windows server 2019 Standard edition in Windows Server 2019 Datacenter Virtual Machine.
I have downloaded ISO file for windows server 2019 and selected Standard edition.
Below Steps performed -
Right click the downloaded ISO file and select 'mount'. Disk(D:) get assigned for the mount.

If prompted with Security Warning, select 'Open'.

  1. Run as Administrator
  2. Upgrade Wizard will open.
    Follow the prompts to complete the Upgrade.
    Install Windows Server page - No change and click 'Next'.
    Applicable notices and licenses terms - Click on 'Accept'
    Choose what to keep - Select 'Keep files, settings, and apps' radio button.
    Ready to install - Click on 'Install'.
  3. System will take 1 to 2 hours for the complete process to complete and reboot. After reboot , I am unable to connect to Virtual Machine. Please help to provide solution of this issue.
Windows for business | Windows Server | Devices and deployment | Set up, install, or upgrade
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  1. Chen Tran 3,205 Reputation points Independent Advisor
    2025-10-06T16:05:57.73+00:00

    Hello Devyani,

    Thank you for posting question on Microsoft Windows Forum.

    Based on the issue description, it seems to be that you are trying to “downgrade” from Windows Server 2019 Datacenter → Standard edition inside the same VM. Unfortunately, I am afraid that Microsoft does probably not support in-place downgrades between editions. This might be the cause that after the reboot, your VM becomes unbootable or inaccessible. Since the installer cannot reconcile the Datacenter feature set with Standard.

    The following are a few of suggestions in an attempt to access to VM.

    1.Restore VM from Backup (if available).

    • If you have a snapshot or backup of the VM before the upgrade, revert to that state.

    2.Perform a Clean Install of Standard Edition.

    • Backup all critical data from the VM (if accessible via recovery tools or ISO).
    • Boot from the Standard edition ISO.
    • Choose Custom Install (not Upgrade).
    • Format the system drive and install Standard edition cleanly.

    3.Use the Hypervisor Console to connect to VM.

    • Open your hypervisor manager like Hyper-V/VMware console.
    • Then, connect to the VM's console view.
    • Log in to the newly upgraded Windows Server 2019 Standard machine using your administrator credentials.
    • Check the VM's status in your hypervisor.

    It is strongly advisable to always verify supported upgrade paths before performing edition changes.

    You can refer to the following article for more information regarding the issue.

    Hope the above information is helpful!

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