I have a ESXi server that I use for testing, however, I am often needing to create additional Windows Server virtual machines.

Typically, if I do not need a VM for more than 30 days, I simply do not activate.

However, I have been doing a lot of HA/DRS testing recently and I have had a few servers up for more than this time.

I have a MSDN account with Microsoft and have already received extra keys for Windows Server 2008 R2. I am doing nothing illegal and I am sure if I asked, they would issue more - but, I do not want to tempt fate!

I have got 3 different "activated" windows snapshots I can get to at any time.

If I try to clone these machines, I get the usual "did you copy or move them VM" message.

If I choose copy, as far as I can see, it changes the BIOS ID and NIC MACs which is enough to disable activation.

If I choose move, it keeps the activation fine (obviously, I know to change the NIC MAC - I believe I can leave the BIOS ID without problems).

However, either of these options keeps the same SID code for the computer and user accounts.

After the activation period has expired, as far as I can see, all that happens is optional updates do not work - it seems that the normal updates work fine. Based on this, as you can easily get in to Windows when not activated without any sort of workaround, I was wondering if it is ok just to leave a machine un activated? (However, I obviously would prefer if it was activated!)

Alternatively, how dangerous is it run multiple machines on a non domain environment with the same SID?

I am just interested to know if anyone can recommend a strategy for me? I have only found one solution that deals with bypassing activation - I am not interested in doing anything remotely dodgy... at a stretch, I am happy to rearm (I have never needed to keep a server past 100 days), but, I would rather have a proper strategy in place.

  • Currently experiementing with VAMT. – William Hilsum Oct 10 '11 at 14:57
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    The limit is 120 days. You can prolong / reset the counter 3 times. Rearm is as good as you get outside a KMS... which you don't get with MSDN. – TomTom Oct 10 '11 at 15:29

Personally, I would use the Move option as opposed to the Copy option.

As far as the SID problem is concerned, maybe this article can address your concerns:


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    Yes basically SID's are not an issue, but duplicate NIC MAC's are (when on the same network at the same time). I've used my MSDN keys many times so you are not limited to just using each one once. Also, when I run out of activations, I DO call them up and they have always given me more. You're using the software for it's legitimate use (temp testing) so I've never been questioned when I tell them I'm reinstalling windows for testing/learning. – Bret Fisher Oct 11 '11 at 2:56
  • We really do prefer that answers have content, not pointers to content. This may theoretically answer the question however, it would be preferable to include the essential parts of the answer here, and provide the link for reference. Thank you! – Chris S Apr 4 '13 at 13:02

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