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

Stefan Falk 266 Reputation points
2020-10-08T15:17:56.87+00:00

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

Windows Server Setup
Windows Server Setup
Windows Server: A family of Microsoft server operating systems that support enterprise-level management, data storage, applications, and communications.Setup: The procedures involved in preparing a software program or application to operate within a computer or mobile device.
241 questions
0 comments

7 answers

Sort by: Most helpful
Most helpful Newest Oldest
  1. Stefan Falk 266 Reputation points
    2020-12-22T12:01:50.723+00:00

    Hello everybody,

    we used the very same script for another customer using VMware and could deploy Windows Server 2019 terminal servers from a template VM with no problem at all. I still have no clue what's going wrong with that one customer where it does not work any more. The next step should be to try to attach the vmdk to another VM to get to the sysprep log files. I'll return here when I have results.

    Best Regards,
    Stefan

  2. Stefan Falk 166 Reputation points
    2022-01-19T15:45:28.877+00:00

    Hello everybody,

    Waltont-9882's posting reminded me to post.

    a) We did not use LAPS there.

    b) The problem got solved once we did not have special characters such as ` and = and ? and ß (a German national character) and " in the local administrator password.

    Hope this helps you, too.

    Best Regards,
    Stefan