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I have a virtualized copy of Windows Server 2008 R2 installed with some applications already installed on it (not server roles) and I would like to re-deploy it on a number of other servers across my enterprise exactly as it is - including the applications installed. I refer to the original disc image as my gold copy.

In the past I have taken a copy of the gold copy and then ran sysprep. Perhaps I am wrong in saying this but I can recollect attempting this previously only to find that after syspreping the image that all applications previously installed were removed after sysprep was completed. Am I correct in stating this happens or do the applications simply need reconfiguring, i.e. in the same manner as an application such as Windows Media Player does after a new user account is created?

I have consulted Microsoft's documentation on sysprep but to say it is poorly organized is an understatement.

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up vote 4 down vote accepted

No, the whole point of sysprep is to strip out the machine-specific settings like activation ID and SID while leaving the installed programs for ease of deployment. Obviously, if certain applications rely on these machine-specific things, they might break, but those are few and far between.

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Thanks for your help – slickboy Nov 19 '12 at 14:25

Sysprep does not remove applications. Some applications are sensitive to sysprep, but those are rare exceptions.

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Thanks for your help – slickboy Nov 19 '12 at 14:24

Most applications should be fine. User configurations will even stick most of the time. There are a few applications I wouldn't run a sysprep on, such as MSSQL, Exchange, or AD. Everything else should be ok. YMMV

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Thanks for your help – slickboy Nov 19 '12 at 14:25

Sometimes, software will look at the machine key or SID as part of a license activation. When you use sysprep on a machine with software like this, the application will stay installed, but you may have to resubmit it's activation.

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Thanks Joel Coel. Do you think its possible this would effect freeware software from Microsoft? Security Essentials For Example. – slickboy Nov 19 '12 at 14:32
@slickboy I don't think so... you don't usually have to activate freeware. It can and will affect Office and Windows, though, which is why most people using sysprep have volume licensing agreements. – Joel Coel Nov 19 '12 at 14:36

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