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Is it possible to upgrade Windows Server 2008 32bit (Web Server) to 64 bit, or would it require a clean install?

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It would require a fresh install.

Windows has never supported a x86/32-bit to a x64/64-bit upgrade in any operating system.

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Thank you Wil . – Mr. Flibble Dec 2 '09 at 18:10
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Ask yourself, would you WANT to play the upgrade game with a MS product like the OS? I can't recall anytime that an upgrade was perfect.

In the old days, of 95-98 upgrades, it would leave bulk behind, or old files, data / garbage.

With a server, I wouldn't play games, reformat, start fresh with a clean slate.

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