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If I am running the 180 evaluation of Server 2008 R2 Standard then wish to purchase the full product will I have to reinstall or will the evaluation activate using my key and all will be well till the end of time?

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The "evaluation" version is the full version with an extended activation period. If you install full product keys it will work without reinstalling. The only requirement is that the evaluation version is an RTM release, not a Beta or Release Candidate.

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Done. I even activated it and it works flawlessly. I just wanted to avoid calling up Microsoft to have to release my key if such a thing was not possible. –  TheLizardKing Jun 9 '10 at 2:08

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