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SYSPREP Tips and Supported Server Roles

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  • If you are trying to reproduce unique virtual machines, always check the generalize checkbox (or use SYSPREP /generalize) to make sure the machine gets a new SID, NIC GUIDs and other identifiers, if you don't, your AD DS will have the impression that you have two of the same machine (since it identifies machines by SIDs) and the situation can get messy. Nonetheless, some features like Windows Network Load Balancing can get confused since multiple NICs have the same GUID.
  • SYSPREP can only reset the Product Activation Key 3 times.
  • Use the sysprep /oobe (which refers to the Out Of the Box Experience), to allow for the custumization fo Windows settings after the reboot
  • Do not use SYSPREP on Upgrade versions of Windows, use it only for clean instalations, the SYSPREP version of each installation of Windows could be different and this can cause trouble
  • Before you SYSPREP a virtual machine, always make sure you are NOT running the CLI for SYSPREP on the Hyper-V host rather than the virtual machine itself :) it happened to me once, but thank God it was in my own testing lab. 

Furthermore, this is a table that includes the roles that are supported for SYSPREP.  If you have to SYAPREP a machine that is intended to host a certian unsupported role, SYSPREP it before the role is installed.

Server Role Sysprep Support

Active Directory Certificate Server (AD CS)

No

Active Directory Domain Services (AD DS)

No

Active Directory Federation Services (AD FS)

No

Active Directory Lightweight Directory Services (AD LDS)

No

Active Directory Rights Management Server (AD RMS)

No

Application Server

Yes

DHCP Server

Yes

DNS Server

No

Fax Server

No

File Services

No

Network Policy and Access Services

No

Network Policy Routing and Remote Access Services

Yes

Print Services

No

Terminal Services

Yes

Not supported in scenarios where the master Windows image is joined to a domain.

UDDI Services

No

Web Server (Internet Information Services)

Yes

Does not support Sysprep with encrypted credentials in applicationhost.config.

Windows Deployment Services

No