Cannot run Sysprep on a Windows virtual machine that was upgraded to a later version

Products

• VMware vCenter Server
• VMware vSphere ESXi

Issue/Introduction

• Cannot run Sysprep on a Windows 2008 R2 64bit Standard virtual machine that was upgraded from Windows 2008 64 bit Standard
• Running Sysprep on a Windows virtual machine that was upgraded to a later version fails
• You see the error:
  
  Sysprep cannot run on a computer that has been upgraded to a new version of Windows. You can only Sysprep on a custom (clean) install version.
  
  
• Manually executing Sysprep from within the guest operating system fails
• The SIDs, hostname, and IP configurations do not change after running Sysprep via the VMware Configuration Wizard

Note: The location of Sysprep in Windows 2008 and 2008 R2 is C:\Windows\system32\sysprep.

Environment

VMware ESX 4.0.x VMware vSphere ESXi 5.0 VMware ESXi 4.1.x Embedded VMware ESXi 4.0.x Installable VMware ESXi 4.0.x Embedded VMware ESX Server 3.5.x

VMware ESX 4.1.x VMware vCenter Server 5.0.x VMware vCenter Server 4.0.x VMware ESXi 3.5.x Installable VMware vCenter Server 4.1.x VMware ESXi 4.1.x Installable

Cause

• This issue occurs because Sysprep can not be used on a Windows operating system that is upgraded to a later version.
• For more information, see the Microsoft article Sysprep (System Preparation) Overview.

Resolution

To workaround this issue:

1. Create a new virtual machine.
2. Perform a fresh installation of Windows 2008 R2 or the guest operating system that you are trying to Sysprep.
3. Clone the virtual machine and perform a guest customization which uses Sysprep to customize the resulting virtual machine.

Additional Information

For additional information about Sysprep, see What is Sysprep?