Not all server roles support Sysprep. If you run the sysprep /generalize command against a Windows Server 2008 installation with specific server roles configured, those server roles may not continue to function after imaging and deployment.
For the Server Roles that do not support Sysprep, you must enable the server role and configure the role settings after imaging and deployment.
The following table shows the list of server roles and whether or not the roles support Sysprep.
Active Directory Certificate Server (AD CS)
No
Active Directory Domain Services (AD DS)
Active Directory Federation Services (AD FS)
Active Directory Lightweight Directory Services (AD LDS)
Active Directory Rights Management Server (AD RMS)
Application Server
Yes
DHCP Server
DNS Server
Fax Server
File Services
Network Policy and Access Services
Network Policy Routing and Remote Access Services
Print Services
Terminal Services
Not supported in scenarios where the master Windows image is joined to a domain.
UDDI Services
Web Server (Internet Information Services)
Does not support Sysprep with encrypted credentials in applicationhost.config.
Windows Deployment Services