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Windows Activation Problem

I'm having a problem with windows activation on two citrix servers that were converted from physical machines to virtual in VMWare.  At random users will not be able to launch citrix apps with a message saying the server's windows license is not activated.  Logging in to the console with administrative credentials allows me to activate but I assume there is a limited number of times this will work.  It was suggested that I try the Windows Genuine Advantage tool which produced the following results:

Diagnostic Report (1.9.0027.0):
Windows Validation Data-->
Validation Status: Validation unsupported OS
Validation Code: 6
Cached Validation Code: N/A
Windows Product Key: *****-*****-33TBK-QPQH2-BRP4Y
Windows Product Key Hash: cbZz1bYjlsuc+nca+2oZdvQXvRM=
Windows Product ID: 69712-012-7506755-44693
Windows Product ID Type: 0
Windows License Type: Unknown
Windows OS version: 5.2.3790.2.00030010.2.0.000
ID: {18850976-ED2D-4297-9D0A-40900C3E175C}(3)
Is Admin: Yes
TestCab: 0x0
LegitcheckControl ActiveX: N/A, hr = 0x80070002
Signed By: N/A, hr = 0x80070002
Product Name: N/A
Architecture: N/A
Build lab: N/A
TTS Error: N/A
Validation Diagnostic:
Resolution Status: N/A
Vista WgaER Data-->
ThreatID(s): N/A
Version: N/A
Windows XP Notifications Data-->
Cached Result: N/A, hr = 0x80070002
File Exists: No
Version: N/A, hr = 0x80070002
WgaTray.exe Signed By: N/A, hr = 0x80070002
WgaLogon.dll Signed By: N/A, hr = 0x80070002
OGA Notifications Data-->
Cached Result: N/A, hr = 0x80070002
Version: N/A, hr = 0x80070002
OGAExec.exe Signed By: N/A, hr = 0x80070002
OGAAddin.dll Signed By: N/A, hr = 0x80070002
OGA Data-->
Office Status: 111 Unsupported OS
OGA Version: N/A, 0x80070002
Signed By: N/A, hr = 0x80070002

I'm not clear on what the error means.  The original server was purchased new from Dell and we did not have this problem until about a month ago.  It has happened several times since then.  I would very much appreciate any ideas on how to solve this issue.
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Ok, I've just found that this tool was not intended for server 2003 which puts me back at square one.  Why would a server 2003 box running citrix presentation server 4.5 need to be activated so frequently?


Also found this in the event log:

An error occurred while the wizard was checking the current Windows product license. Error Code: 0x80040507
Solutions Architect
The problem you are having is that you started off with an OEM Server License, which licenses the OS for that Physical Machine. If you read the EULA, the license *CANNOT* be transferred to a new machine.

You have no other choices with 2003 other than a re-install of the OS with a different license.

<--SERVER 2008-->
I typed all this up thinking that this was a 2008 box, then I re-read the question and saw it was 2003... so if any of you are having problems on a 2008 install, the following applies:

The 2008 OEM license comes with a single virtual server license, that if you change your product key to the virtual instance of the OEM license, then you should be able to activate properly.  

The server is having a problem reconciling that it is no longer a physical box. When virtual components activate, it will invalidate your activation.  Truth be told, your box should have never activated in the first place once it was virtualized, but apparently enough of the physical machines signature was kept that it allowed it to happen.

If plugging in the different key does not work, I would recommend you snapshotting the server, then running SYSPREP C:\windows\System32\sysprep


Ok, I see what you are saying but I'm just amazed that the P2V process invalidates the OS license.  Is there a safe way I can switch to another product key that will work on a virtual machine?


I did some reading and I think you're exactly right, thank you very much.  I've read that one option is to do a repair using volume license key media but it seems like I'm likely to have problems with citrix or the installed applications after.  It is in VMWare so I'll have to experiment.  Thank you again for your quick answer!