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Most people don’t realize that if you change the hardware (motherboard, network card, etc) in your desktop computer that Windows switches back to unactivated/unlicenced mode. AfterI replaced the motherboard in my desktop Microsoft actually told me that I had to buy a whole new Windows 7 license (because my Windows 7 OEM product was locked to the motherboard). Sadly this is where the software industry has gone; I understand the need for it, but I don’t like.
When I moved HAAst new a new server it too switched to unactivated/unlicensed mode. I emailed the folks at HAAst who sent me a new license file. So don’t worry – its painless. (Unless you are dealing with Microsoft, which is always painful).
I think painfulness of activation/licensing really comes down to the attitude of the vendor. My experience with the folks at HAAst has always been great.