Windows Server 2008 R2 Datacenter OEM–Different in “key” ways


Woody Walton 2010

Woody Walton

I love Windows Server 2008 R2!  Like you, I especially love the advanced capabilities resident in the Enterprise and Datacenter editions.  I imagine those of you out there pitching virtualization, high availably, and other similar solutions sell it frequently.  Of course price matters and you may be inclined to recommend to your customer less expensive purchasing options for those server skus, as they carry a higher price tag.  If you are buying Hardware from HP, Dell, or others through distribution or direct, you can purchase that server with an OEM version of Windows Server 2008 R2. Any of the versions of Windows Server (Standard, Enterprise, Datacenter, SBS, and even HPC.) are available via OEM and sales reps at the manufacturers (if you buy direct), or at the distributors are happy to add OEM Windows server to your invoice!  What could be better?  A simple transaction, you saved your customer money.  It all looks good so far.

Of course you know by the title there is a catch!  …There is always a catch!  You may think that you know what the catch is already, but perhaps you don’t know this one.   It goes without saying that OEM software is tied to the hardware that it is purchased with.  To quote the Windows Server 2008 R2 Licensing Guide:

“With a license purchased with a server from an OEM, the Windows Server license is already
assigned to that specific server, and lives and dies with that server. The OEM end
customer is not allowed to reassign that OEM license to another server.”

As long as your customer is fine with that, you are good to go!    

MAYBE!!!  …Let me illustrate.  The devil is in the details.

We are not quite out of the water yet.

When we start speaking of the Enterprise and Datacenter editions which confer virtual licenses as well, we start to see some other implications that are not as well known. 

I recently had a situation come to my attention where a partner was getting this error when they attempted activate the virtual machine images they had created for a customer’s virtualized and consolidated environment:

key issue


So why did this occur?  The partner was using the Product IDs (keys/ PIDs) supplied with the OEM media (Datacenter comes with both a physical and virtual key).  Neither would work.   In following up with this partner it was discovered that they had used a normal Windows Server 2008 R2 Standard media or ISO to built the image.   If this was a volume license version of Datacenter this would not have been a problem because they could have used KMS or MAK keys  supplied by Microsoft.   more on MAK and KMS activation can be found here.

So they were using the key supplied with the OEM datacenter media to attempt to activate another type of base media, thus the error.  OEM datacenter is different in that you MUST use the supplied OEM media for ALL images /virtual machines or physical installs on that server.

to repeat, OEM installation media must be used to install the operating systems in order to use the OEM licenses and keys supplied.

The partner did not know this beforehand and it caused a lot of lost cycles recreating the virtual machine images and re-deploying them.  This knowledge aside, the partner likely used another Windows Server 2008 R2 Standard media because 1.) it was handy, or 2.) they did not know that the Windows Image File format in Datacenter includes all subordinate versions of the OS (on the same media). So Datacenter media includes the ability to create images for Standard, Enterprise and Datacenter.  Armed with a little knowledge about our WIM format might have saved them all the trouble in the first place.

The intention of this post is not to provide a primer on imagex.exe which is available in the Windows AIK (automated installation kit), but rather to let you know that media has a lot more on it than you might think.

Simply running the “imagex /info” command on the install.wim file in the sources directory of the media you have present will tell you all you need to know.  The GUI based tool in the aforementioned Windows AIK will provide similar info, albeit not as quickly.

Fully testing these virtual machines/images before deploying them en masse would have caught this sooner.   Learning through experience is the best way to learn and as we all know experiences like what I mentioned here can be painful.   It is always nice to go to school on someone else.

Incidentally, if you ever have questions about licensing and you are a partner, please call our licensing desk at 1-800-426-9400.   They have licensing experts who know the specifics of all of our licensing model.  …It is where I went to get the answer! Winking smile





Comments (2)

  1. james says:


    Regarding this post, from the screenshot it appears that you show an attempt to activate 2008 R2 Standard with a Datacenter key, which I would expect to fail.

    However your post reads that if you install Datacenter using VLK media, an OEM Datacenter key will not be accepted by windows activation?

    Could you clarify please?


  2. Gianluca A. says:


    can you explain better the way to use the DC key code on "child" STD or ENT installation?

    In the DVD of DC is present the full installation for ALL O.S. version, but unfortunately I'm not able to activate in any way the STD and ENT installation.

    I'm looking forward a good news from you.

    A little HOW TO is very appreciated.

    Thank you.


    Gianluca A.

Skip to main content