Preparing Windows Server OS for activation

Activation of a trial version of Windows Server using Enterprise keys.

These instructions are for use if the operating system notifies you that the system version is incompatible with your key when you try to activate the Windows Server 2012/2016 operating system running in the cloud and have entered a valid key.


To solve problems of this type, first complete a number of simple actions.

  • Deploy the instance from the image you require.
  • Run the instance and connect to it via the console or RDP.
  • Execute the command line with the administrator rights.
  • Press the Win key (the key with the Windows symbol) + X on the keyboard and then select ‘Command line (administrator)’ from the menu that appears. You can also display the same menu by right-clicking on the Start button.
  • Execute the following sequence of console commands, which remove the evaluation version of the OS and thereby prepare it for licensing:
  1. Check current edition of OS:
C:\>DISM /online /Get-CurrentEdition
DISM system
Version: 10.0.14393.0
Image version: 10.0.14393.0
Current edition:
Current edition: ServerStandardEval
Operation completed successfully.

The output of the command DISM /online /Get-CurrentEdition indicates that the current OS version is the - ServerStandardEval.

  1. Check for the available editions for the OS currently installed:
C:\>DISM /online /Get-TargetEditions
DISM system
Version: 10.0.14393.0
Image version: 10.0.14393.0
Editions that can be updated to:
Final edition: ServerStandard
Final edition: ServerDatacenter
Operation completed successfully.

For the current OS release, only ServerStandard and ServerDatacenter are available. Accordingly, you can only perform licensing for these two OS editions.

  1. To change the OS from the evaluation version to the trial version, execute the following command: DISM /online /Set-Edition:<edition ID> /ProductKey:XXXXX-XXXXX-XXXXX-XXXXX-XXXXX /AcceptEula
    • edition ID - is the available required OS release;
    • ProductKey:XXXXX-XXXXX-XXXXX-XXXXX-XXXXX - is the key for the retail product.
    • ProductKey для ОС Windows (Windows Vista - Windows Server 2016) is available on the official resource MS Windows.
    • ProductKey для ОС Windows (Windows 7 - Windows Server 2019) is available on the official resource MS Windows.


C:\>DISM /online /Set-Edition:ServerStandard /ProductKey:WC2BQ-8NRM3-FDDYY-2BFGV-KHKQY /AcceptEula
DISM system
Version: 10.0.14393.0
Image version: 10.0.14393.0
Starting update of components...
Starting setup of product key...
Setup of product key completed.
Delete package Microsoft-Windows-ServerStandardEvalEdition~31bf3856ad364e35~amd64~~10.0.14393.0
[=====                      10.0%                          ]

After launching the above command, the process of preparing the OS for replacing the evaluation version begins. It may take some time for the process to complete.

Once the command is successfully completed, the system generates a notification recommending a reboot of the OS:

Delete package Microsoft-Windows-ServerStandardEvalEdition~31bf3856ad364e35~amd64~~10.0.14393.0
Update of components completed.
Applying release parameters...
Application of release parameters completed successfully.
Operation completed successfully.
To complete this operation, reboot Windows.
Do you wish to restart the computer now? (Y/N)
  1. The OS restart must be confirmed by pressing ‘Y’.
  2. After restarting, perform a second check of the OS release version:
C:\>DISM /online /Get-CurrentEdition
DISM system
Version: 10.0.14393.0
Image version: 10.0.14393.0
Current edition:
Current edition: ServerStandard
Operation completed successfully.

It can be seen from the output of the command that the process of changing the OS edition was successful and the system is ready for licensing.


Before activating the OS, it is essential to check that all date and time settings are up to date. If the date or time are not up to date, the activation process may result in an error. We recommend that you synchronise the date and time using the Windows OS functionality.


Pay particular attention to the fact that deploying infrastructure in the cloud using the Windows Server OS may result in certain difficulties at the point of licensing the operating system.

The difficulties may arise with the installed AD (Active Directory) roles or Windows Exchange, which do not allow the evaluation version to be uninstalled, yet this is a necessary procedure before being able to activate the Windows OS. This peculiarity may result in the need for certain roles and software to be deleted beforehand, then for the edition to be changed, and only then to proceed with re-installing the required roles or activating the OS.

We recommend that you replace the evaluation version with the version required and continuing straight away with setting up the server.

Why does Windows not activate itself automatically, immediately the licence is purchased?

The need to execute a special command is due to the particular technical requirements involved in upgrading the evaluation version of Windows Server to the full retail version. Without the user’s intervention the OS is unable to determine the ID of the release or the product key. If you require help with activation, please contact our customer support department.

By default, all Windows OS images prepared for installation are offered without pre-installed commercial licences. At the step of preparing the images, a temporary official evaluation licence is used. The licensing of the software used is the sole responsibility of the client.


After the expiry of the evaluation period, if you are still using an evaluation licence, Windows may periodically reboot. Such reboots are self-activated and reflect Microsoft’s policy. In such situations we always recommend that you activate your own copy of the OS.

You can obtain the licences manually, use existing licences that you obtained previously, or use the services of SIM-Networks to obtain them.