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I have a VM configured with internal software that needs to be sent to an outside party for evaluation. As it stands, the user who configured it also activated the software with a company issued MSDN key, something I don't want to be sending outside the organization.

Sysprepping the image does seem to prompt for a new key on startup but can be skipped and, surprisingly, still permits activation with the previously used key.

Is there a way to remove the key completely and force the recipient to activate the OS by their own means? Is there another way to accomplish this outside of a rebuild on an unactivated clean install?

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up vote 5 down vote accepted

Specify the KMS Client Setup Key in the sysprep answer file. Here's a list of keys for WS 2008 R2:

Windows Server 2008 R2 HPC Edition - FKJQ8-TMCVP-FRMR7-4WR42-3JCD7
Windows Server 2008 R2 Datacenter - 74YFP-3QFB3-KQT8W-PMXWJ-7M648
Windows Server 2008 R2 Enterprise - 489J6-VHDMP-X63PK-3K798-CPX3Y
Windows Server 2008 R2 for Itanium-Based Systems - GT63C-RJFQ3-4GMB6-BRFB9-CB83V
Windows Server 2008 R2 Standard - YC6KT-GKW9T-YTKYR-T4X34-R7VHC
Windows Web Server 2008 R2 - 6TPJF-RBVHG-WBW2R-86QPH-6RTM4

This will give them a 30 or 60 day grace period (provided you rearm the machine during sysprep) before forcing them to enter their own key (unless they run their own KMS server, in which case, it will just activate for them).

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