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I have a new dedicated server, but my host charges €10/month to have a Windows 2008 R2 Standard OS installed. I require Windows Server 2008 R2 Datacentre primarily because of the networking features, however the host also does not offer this.

As I already have a (legal) copy of Windows Server 2008 R2 (all editions- Microsoft Dreamspark), it's only natural that I do not want to pay €10/month for software that I already own.

So I was thinking, I know the first half of the Windows Server installation can be done via Wine, but as soon as the server restarts, I will lose access (obviously) as the Windows Server installation will start. I'm able to reinstall Linux if things don't work, so I can ultimately reinstall Linux should there be an issue (this is free).

The one way I can do it is via a KVM, but the host doesn't offer this either. Remote Desktop is essentially the same as a KVM (minus the 'video' bit).

My question is, it is possible to configure the Windows Server 2008 R2 image to automatically set-up RDP, so that I could access the Windows Server 2008 R2 installation when it reboots? I've checked with another host, and they told me that I can give them my serial key and they will install the OS without any cost, so why can't my current host do this? The server is free for a month, which is why I'm going with this host.

So basically, is it possible to set up RDP so that I can access the server computer via RDP when the Windows Server 2008 R2 installation takes over when the server computer reboots?

The current OS is Ubuntu 12.02LTS, with 2x 1.5TB hard drives (not in RAID, they're completely separate).

share|improve this question
If you are renting a VM, you should have access to the VM's console and video display. You can't RDP in during the Windows Setup Process, you need to be able to see the VM's virtual screen. – heavyd Mar 19 '14 at 19:16
@heavyd It's not a VM; this is a full dedicated server. – cybermonkey Mar 19 '14 at 19:18
It can work, and there are guides to do it. If you run into any problems though you're stuck, so you might want to dry run the process on local hardware so you can figure out what you need to do to make it work. See… – heavyd Mar 19 '14 at 19:22
There are ways to create an unattended installation for Windows all you have to do is boot to the installation media and all installation options are choose for you – Ramhound Mar 19 '14 at 19:45
You would need to configure grub to boot once to the installation disk either through a script or something the modify it after windows is installed – Ramhound Mar 19 '14 at 19:52

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