After we have allowed Windows 2008 Servers in our VMware VI enviroment, we been having problems sysprepping Windows 2008 Server.
So here is a quick guide to sysprep a Windows 2008 server in a VMware VI enviroment.
(Use this workaround until VMware VI allows you run sysprep against a WIN2008 Server)

  1. Change the source or templates Guest Operating Systemsetting to “Vista (32 bit)” or “Vista (64 bit)” depending on the installation of the Windows 2008 server installation.
  2. Clone the VM or template and you are now able to customize your Win2008 server with sysprep.
  3. After the cloning is done Power On the new VM and let the customization complete.
  4. Shutdown the VM and change the Guest Operating Systemsetting back to “Windows Server 2008 (32/64 bit)”

The reason the above workaround works is that Vista and Server 2008 has sysprep build into the OS and the sysprep in both OS’s and are based on the same technology.

Read more here

http://www.vmwareinfo.com/2008/05/sysprep-windows-2008-in-vmware.html

http://communities.vmware.com/message/934733#934733

http://technet.microsoft.com/en-us/library/cc766514.aspx