Is there an upgrade path from Windows Server 2008 Standard SP2 (not R2) to any 2012 edition? I'm open to workarounds, but I'm trying to upgrade out of 2008 without having to reinstall and reconfigure existing software and files.
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Is your Windows Server 2008 machine running an x64 or x86 version? – Evan Anderson Jan 29 '14 at 20:11
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The x64 version – Keith Jan 29 '14 at 20:35
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Yes, you can upgrade to the non-R2 edition of Windows Server 2012.
http://technet.microsoft.com/en-us/library/jj134246.aspx
If you are running:
Windows Server 2008 Standard with SP2 or Windows Server 2008 Enterprise with SP2
You can upgrade to these editions:
Windows Server 2012 Standard, Windows Server 2012 Datacenter
Then if you want to upgrade to 2012 R2 from regular 2012 you can do that whenever.

TheCleaner
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It doesn't explicitly mention it, but I would imagine that it's not possible to upgrade from the 32-bit version of Server 2008. – Chris McKeown Jan 29 '14 at 20:04
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Ah, it does in this article here: http://technet.microsoft.com/en-us/library/jj574204.aspx – Chris McKeown Jan 29 '14 at 20:05
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