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Is it possible to upgrade to Windows Server 2012 R2 from Windows Server 2008 R2? Our Windows Server 2008 R2 has a valid license key.

I do not have the installation media for Windows Server 2012 R2. If I download the Windows Server 2012 R2 Evaluation installer, will it recognize my Windows Server 2008 R2 license keys?

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For the first question, Yes, but some of the configuration will lost.

For your second question, sadly, your Windows Server 2008 R2 licence cannot be used to activate a copy of Windows Server 2012 R2. And the evaluation installer may not contain the image of a retail or volume licencing version installer.

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    So does this mean that I have to buy a new license for the newer Windows Server OS? – F0r3v3r-A-N00b Apr 10 at 9:44

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