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I was wondering if I could I install a wallet on Windows Server 2008? If so which wallet?

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You can install "Bitcoin-Core" (including Bitcoin-Qt) on a window server 2008. It requires initial syncing and verification of around 40GB of data. So it might take 1-2 days until you can use it.

Other option would be to install a SPV client like "Electrum" (Python based) or "Multibit HD" (Java / bitcoinj based). They can be used immediately but they won't give you the same level of privacy.

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