Convert Windows Server Evaluation Editions to Standard

Upgrading Windows Server without reinstalling

(as of this post, the newest version is Server 2019)

If you have an evaluation version of Windows Server  and you wish to convert it from an evaluation version to a standard or datacenter version, it's pretty straightforward. (If you have any domain controllers set up you'll have to demote them first, but after the conversion, you can promote them again.) you merely need to:

• Open an elevated command prompt and type the following command to find the available edition IDs: 

    DISM /online /Get-TargetEditions

• Decide which one you want and copy that ID. You'll use it to replace <edition ID>
• go to Windows KMS keys to find the Generic Volume License Key (GVLK) for that version or have your own purchased key handy. You'll use it to replace XXXXX-XXXXX-XXXXX-XXXXX-XXXXX
• type the following command (all on the same line - it wraps to the next line on this blogpost), substituting the correct edition ID and Product Key

DISM /online /Set-Edition:<edition ID> /ProductKey:XXXXX-XXXXX-XXXXX-XXXXX-XXXXX /AcceptEula 

The Edition ID will be either ServerEssentials, ServerStandard or ServerDatacenter, and you can either provide your purchased product key for that edition, or use the GVLK (Generic Volume License Key - which you can find from the link provided below).  The server will run through the image conversion process, then restart once or twice. 

After the server has fully restarted, you will need to re-activate the server and enter the Key again, or use another activation method.

Ethics

You can skip to the notes if you don't have any

Obviously if you want to bypass activation, you could use something similar to Microsoft Toolkit (which no longer works). I don't recommend that course of action for several reasons:

1. It is a security risk for your server and provides back-door access to the operating system for the activation bypass process.
2. Finding a method that works could be very time consuming.
3. Any decent antivirus program will see it as a threat and remove it, thereby deactivating your product. 

As far as my third point is concerned, you can no longer just turn off your antivirus program (which you should never do anyway), but you could temporarily turn it off and add exceptions in your antivirus program - both of which leave the server vulnerable. Really, who knows how long it will be before some hacker finds an exploit through this vulnerability (which you would have just introduced) or until Microsoft finds some way to block it?

Keep this in mind: any time you bypass official protocols you do so at your own risk (and your clients' if you are selling these services).

Some other points to consider:

• What's the risk to your data, reputation and finances?
• Who could it affect?
• What kind of damage could there be?
• What are the possible repercussions?
• What will you do if you are found responsible for damages and held accountable?

Notes

You have to open a command window as administrator to use the following.

To get your current edition:

DISM /online /Get-CurrentEdition

To get the available versions:

DISM /online /Get-TargetEditions

examples:

Target Edition : ServerStandard

Target Edition : ServerDatacenter

Target Edition : ServerEssentials

To find the appropriate GVLK:

Windows Server 2019 Product Key: See this site: Windows KMS keys

To change the version:

DISM /online /Set-Edition:<edition ID> /ProductKey:XXXXX-XXXXX-XXXXX-XXXXX-XXXXX /AcceptEula

example:

The following example worked when I looked up the appropriate key from the link above and tested on my evaluation version of Server 2019:

DISM /online /Set-Edition:ServerDatacenter /ProductKey:WMDGN-G9PQG-XVVXX-R3X43-63DFG /AcceptEula

Credits

Thanks to the following website for their article which formed the basis of this blog post:

https://www.pei.com/2018/04/upgrade-windows-server-evaluation/