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With Windows 2000/XP, possibly NT4 even, we used to copy the i386 folder to %SYSTEMROOT%, usually c:\windows, and update a key within HKLM\Software\Microsoft\Windows\CurrentVersion\Setup to point to that. Then when Windows Setup needed something from the disk it would look there before asking for the CD. Is that even necessary with Windows 2008 Server? Or more specifically, is there ever a scenario that will ask for the install DVD anymore or will it always pick from WINSXS?

I'm looking to avoid the old scenario of performing remote maintenance only to find that I need to drive into work just to pop a DVD in.

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You do not need to copy the install files from the DVD to the server after installation. Windows Server 2008 and up already does this for you. When you select a role to install all the bits are already there, they just have to be turned on. This is also why the default installation of Server 2008 and up is so much larger than the previous servers...you have the setup files copied.

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In theory, one doesn't need the DVD any more after the initial installation of Server 2008.

However, in practice one can never be sure with Microsoft, and you also might find that you need some stuff from some other folders of this voluminous DVD.

The best solution is to convert the DVD to an .iso file, so as to mount that file for these rare cases where the DVD is still required, to avoid driving into work.

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