Posey's Tips & Tricks
Bringing an Evaluation Server into Production
Brien Posey explains how to convert an expired Windows Server evaluation VM into a production server using DISM and proper license activation steps.
As someone who writes about technology for a living, I find myself constantly setting up Hyper-V virtual machines as a way of experimenting with various Windows features. Most of the time, these virtual machines only stick around for as long as it takes me to finish whatever assignment I happen to be working on. Recently though, I had something unexpected happen.
I had been working on a project related to Windows Server and had deployed Windows Server 2025 using an evaluation license. When the project was done however, I decided to bring that particular virtual machine into my production environment (it's a long story).
Normally, if something like that had happened, I would have just deployed a brand new virtual machine to use in production. However, I had already gone through all the trouble of configuring this particular virtual machine and given how busy I have been lately, I really didn't want to have to take the time to delete the VM, just to deploy yet another VM that was exactly like the one that I just deleted.
I have to admit that I thought that the process of bringing the VM into my production environment would be super simple. I assumed that I would be able to enter a license key, activate the server, and that would be the end of the process. In reality, that turned out not to be the way that the process works.
The first obstacle that I ran into was that the option to enter a product key was grayed out. As such, I had to resort to entering the product key from the command line. Of course, that's normally easy to do. The command is:
slmgr.vbs /ipk XXXXX-XXXXX-XXXXX-XXXXX-XXXXX
In this case though, Windows kept rejecting my product key. As it turns out, the reason why my product key was being rejected was because coincidentally, the evaluation license had expired just prior to me trying to license the server. When that happens, Windows won't accept a product key, period.
The trick to being able to license a server that is currently using an expired evaluation license is that you have to convert the license before you can enter a product key. To get started, enter the following command into an elevated PowerShell session:
DISM /online /Get-CurrentEdition
This command will show you the current Windows Server edition. You will probably see something like ServerStandardEval or ServerDatacenterEval. This confirms that the server is indeed using an evaluation license that will need to be converted prior to licensing the server.
The next step in the process is to gather a list of target Windows Server editions. These are the editions that you can potentially convert the license to. The command used to reveal the target editions is:
DISM /online /Get-TargetEdition
When you enter this command, you should see the target editions listed. As an example, you might see ServerStandard and / or ServerDatacenter.
Now that you know what edition is currently running and what edition you can convert the license to, you will need to use the DISM command to convert the license. In order to complete this step, you are going to need to use a generic conversion key (do not enter your real product key yet). As an example, if you are converting Windows to Server Standard, then the command that you will use looks like this:
DISM /online /Set-Edition:ServerStandard /ProductKey:XXXXX-XXXXX-XXXXX-XXXXX-XXXXX /AcceptEula
If you are going to be converting Windows to use Server Datacenter, then the command will look like this one instead:
DISM /online /Set-Edition:ServerDatacenter /ProductKey:XXXXX-XXXXX-XXXXX-XXXXX-XXXXX /AcceptEula
In both of these commands, the product keys have been omitted. As previously noted, you will have to use generic product keys that are supplied by Microsoft. Fortunately, Microsoft publishes these keys online. You can find the generic product keys here.
When you are done, reboot Windows to finish switching editions. The only thing left is to enter your real product key, by using this command:
slmgr.vbs /ipk XXXXX-XXXXX-XXXXX-XXXXX-XXXXX
When you are done, you should be able to activate Windows.
About the Author
Brien Posey is a 22-time Microsoft MVP with decades of IT experience. As a freelance writer, Posey has written thousands of articles and contributed to several dozen books on a wide variety of IT topics. Prior to going freelance, Posey was a CIO for a national chain of hospitals and health care facilities. He has also served as a network administrator for some of the country's largest insurance companies and for the Department of Defense at Fort Knox. In addition to his continued work in IT, Posey has spent the last several years actively training as a commercial scientist-astronaut candidate in preparation to fly on a mission to study polar mesospheric clouds from space. You can follow his spaceflight training on his Web site.