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We have a remote server running windows 2008 Enterprise but looking to upgrade to R2 - will this work using remote desktop to the server or will we have to go and get the server out of the rack / add a monitor and keyboard to the server? Don't want to start the install / upgrade and then discover it hasn't worked!

Thanks in advance

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Yes you can but you'd have to be familiar with the microsoft deployment toolkit. I've done clean installs headless but not an upgrade ( but frankly I would never upgrade a server if I could avoid it).

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I suspect a MDT-guided installation is not what the original poster had in mind when saying "will this work using remote desktop" :-p – Massimo Sep 1 '09 at 18:31
I would suspect it is since he doesn't have a mouse or keyboard attached and he wants to do a remote install – Jim B Sep 1 '09 at 19:12
yes thats right - want to do a remote install without dragging everything out but since not familiar withe the mdt, a visit to the rack may be in order! – jamie Sep 1 '09 at 19:33
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Windows Server 2003 R2 was an add-on to Windows Server 2003, so you could install it on an existing system without any particular issue.

Windows Server 2008 R2 is a new release of Windows Server, so it requires a full operating system upgrade, like going from Windows Vista to Windows 7.

This just can't be done remotely.

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