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I'm running Windows Server 2008 R2 (via Rackspacecloud) and now that I'm going live I'm just curious if there are any security settings I should "turn on" or other settings I should tinker with to make it 90~95% secure?

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You should harden your installation, Microsoft has a Security Guide for Server 2008 (which also applies to R2). See the additional resources on that page as well for more information, especially the Solution Accelerators.

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