Hello JustATech401,
Thank you for posting in Microsoft Community forum.
Regarding your issue with Sysprep on a Windows Server 2019 VM, it is possible that the "SkipUserOOBE" setting is enabled in the unattend.xml file. This setting can cause the administrator password prompt to be skipped during the OOBE process.
To resolve this issue, you can try the following steps:
- Open the unattend.xml file in a text editor.
- Search for the "SkipUserOOBE" setting.
- If it is set to "true", change it to "false".
- Save the changes to the unattend.xml file.
- Run Sysprep again with the updated unattend.xml file.
If the issue persists, you can also try creating a new unattend.xml file with the Windows System Image Manager (SIM) tool and ensure that the "SkipUserOOBE" setting is set to "false".
I hope the information above is helpful.
If you have any question or concern, please feel free to let us know.
Best Regards,
Haijian Shan