It turns out that Microsoft, in its wisdom, decided to limit the number of times that a Windows image can be syspreped to just three. The fourth time someone runs sysprep the process fails. This has to do with resetting (re-arming) of the licensing information. There are a few workarounds to this, one involving creating an unattended installation xml file. I’ve found the following to be the quickest and easiest:
Once the master image is ready to be syspreped open command prompt and run slmgr /dlv
You will see the following screen:
If you see that the remaining windows rearm count is at 0 you will need to edit the registry to trick Windows into thinking that it has one more rearm available.
Re-run sysprep and it should complete.
Once you run sysprep, the SkipRearm registry value will change back to 0
In some instances you may also need to change the value of the Generalization State key.
Go into the registry and set HKEY_LOCAL_MACHINE\SYSTEM\Setup\Status\SysprepStatus\GeneralizationState to 7.
Re-run sysprep and it should complete.
Once you run sysprep, the SkipRearm registry value will change back to 0
In some instances you may also need to change the value of the Generalization State key.
Go into the registry and set HKEY_LOCAL_MACHINE\SYSTEM\Setup\Status\SysprepStatus\GeneralizationState to 7.