Note that this guide also applies to Windows Server 2016 and Windows 10.

You might have to evaluate Windows Server 2019 for your company or organisation or even for personal use, to see if it fits your use-case before committing to it. Of course no one wants to buy expensive software to then find it out it’s not the right thing. So, today I will show you how to obtain a free trial and how to upgrade it to the full version once you decided it’s the right thing for you or your organization.

Obtaining Windows Server 2019 Trial (Evaluation)

To get the free trial of Windows Server 2019 head over to Microsoft’s Evaluation page here and choose the the desired version.

If you want Windows Server 2019 Standard or Datacenter, simply chose “Windows Server 2019” as you will be able to choose between the editions during installation. You will also be given the choice between Core and Desktop Experience (GUI).

You will be asked to fill out details in a form, do so, and then proceed to downloading the “ISO” file. This is the installation medium which can then be burnt to a DL-DVD, USB drive or installed in a VM.

The ISO file (installation medium) is about 5 GB in size.

Installing Windows Server 2019

Simply burn the ISO to a DL-DVD or USB drive for installation then insert the medium into the machine (or mount the ISO in the VM) and proceed to installing it as you would install Windows 10. When asked for the edition, choose your desired one. If you want a GUI make sure to choose the edition with “Desktop Experience”. In this example we’ll go for Windows Server 2019 Datacenter with Desktop Experience.

After successful installation, you will have 180 days (six months) for evaluation.

If you’re installing on a VM, make sure to install your VM provider’s guest additions (drivers/tools).

Upgrading To The Full Version

Once you decided Windows Server 2019 is right for you, you can obtain (purchase) a product key from Microsoft to upgrade to the full version.

I will show you how to upgrade the trial to the full version and then how to activate it with your product key. This also works with a KMS key and KMS server.

So make sure you have:

  • A product key for your edition of Windows Server 2019 or a KMS server with the correct license set up
  • An active internet connection and enough bandwidth
  • Admin access to the Windows Server either through RDP or OpenSSH or some other means (you need to run a CMD or PowerShell as admin)

In the admin CMD type:

dism /online /get-currentedition

To view your current edition. In our example this will return “ServerDatacenterEval” which has the “Eval” at the end, which means it’s the trial. We want to upgrade to the full version.

Now type the following command to see the possible targets to upgrade to:

dism /online /get-targeteditions

In our example this will output “ServerDatacenter” which is the full version (no “Eval” at the end). This is the edition we want.

To upgrade to that version, you need a valid product key or a KMS key. In this example we’ll be using a KMS key, so type the following:

dism /online /set-edition:ServerDatacenter /ProductKey:WMDGN-G9PQG-XVVXX-R3X43-63DFG /AcceptEula

Make sure to replace the edition with the desired one from the list output of the previous command. Also make sure to set the correct product key.

Which will output something like:

Starting to update components...
Starting to install product key...
Finished installing product key.

Removing package Microsoft-Windows-ServerDatacenterEvalEdition~31bf3856ad364e35~amd64~~10.0.17763.1
Finished updating components.

Starting to apply edition-specific settings...
Finished applying edition-specific settings.

The operation completed successfully.
Restart Windows to complete this operation.
Do you want to restart the computer now? (Y/N)

If you can, restart the server by hitting Y. Otherwise hit N and schedule the reboot for when possible.

After the restart you can use dism /online /get-currentedition again, which should show the full version.

You can activate your copy of Windows Server 2019 in an admin CMD by typing:

slmgr /ato

If you used a proper product key it should activate. If it was a KMS key and the KMS server is defined in the DNS, it should also activate.

If the KMS server is not in the DNS, you can specify it manualy with:

slmgr /skms YOUR_KMS_ADDRESS

Now run the activation command again, and if your KMS server is set up correctly it should activate.

That’s all there is to it!

Getting KMS Keys

Microsoft provides a list of KMS keys here which can be useful to upgrade and then activate later.