Sysprep of a Windows Server 2019 leads to a machine where we cannot logon

Question

Hello everybody,

we routinely deployed Windows Server 2016 terminal servers by cloning and sysprepping them from a template (using a PowerShell script). The very same with Windows Server 2019 fails, and even if we manually just clone the template VM, start it (disconnected from the network), sysprep it (OOBE, generalize, reboot), the following symptoms occur:

1) Sysprep takes 15 - 20 minutes (compared to, say, 5 minutes normally)

2) Sysprep does not ask for a new local Administrator password.

3) The machine boots, but we cannot log on a s a local Administrator. This is regardless of whether we

• clone and sysprep manually,
• include a C:\Windows\Setup\Scripts\SetupComplete.cmd with "net user administrator /active:yes" in the template (see https://kb.vmware.com/s/article/2034622), or
• use our PowerShell script which normally injects a fixed Administrator password via the sysprep answer file.

Has something changed in sysprep's behaviour between Windows Server 2016 and 2019?

Best Regards,
Stefan Falk

Answer 1

Hello PieseFordro,

Thank you. Yes, that is exactly what we do normally. We have sysprepped many servers at many customer's sites both manually and automatically. The point is really simple here:

1) A freshly installed machine.
2) Sysprep it with no customization file at all.
3) The result is a machine on which you cannot logon using the local Administratory account.

And we wonder what could be wrong, as there should hardly be an opportunity to make a mistake here.

Best Regards,
Stefan

Answer 2

Hello Stefan,

Please understand that VMware is not Microsoft product, if you want to use vmware to deploy Windows Server 2016 terminal servers, you’d better ask for help from vmware support.
Go back to sysprep, manually sysprep server 2019 has nothing different with server 2016, normal processes are:

1. Installing Windows Server 2019 onto a new server
2. Configuring customizations and updates onto your new server
3. Running Sysprep to prepare and shut down your master server
4. Creating your master image of the drive
5. Building new servers using copies of the master image
   Or use unattended file
6. Create unattendfile with Windows System Image Manager.
7. Copy your unattendedfile.xml file to the \system32\sysprep folder
8. Run CMD as Administrator
9. sysprep.exe /generalize /oobe /unattended:yourunattendedfile.xml
   Next, you could Add a Custom Script to Windows Setup
   https://learn.microsoft.com/en-us/windows-hardware/manufacture/desktop/add-a-custom-script-to-windows-setup

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Answer 3

Hello TeemoTang,

Thanks for your input.

As to avoid the VMware provisioning or our PowerShell provisioning script, we tried to just make a copy of the VM and sysprep it totally manually. To I think we have no cause to assume the problem is related to VMware. We are, of course, aware, that Microsoft could not support a VMware case.

The question remains: What could be wrong with the Windows Server 2019 machine that would cause sysprep to somehow result in an unknown local Administrator password or a disabled local Administrator account?

Best Regards,
Stefan

Answer 4

These steps are best
1.Installing Windows Server 2019 onto a new server
2.Configuring customizations and updates onto your new server
3.Running Sysprep to prepare and shut down your master server
4.Creating your master image of the drive
5.Building new servers using copies of the master image
Or use unattended file
1.Create unattendfile with Windows System Image Manager.
2.Copy your unattendedfile.xml file to the \system32\sysprep folder
3.Run CMD as Administrator
4.sysprep.exe /generalize /oobe /unattended:yourunattendedfile.xml
Next, you could Add a Custom Script to Windows Setup

Answer 5

Hello PieseFordro,

If it cannot be answered why the machine is left unusable by sysprep, is there a way to get to the sysprep log? I guess we could only attach the virtual disk to another, running machine and look there, right?

Best Regards,
Stefan