Upgrading Windows Server 2019 Evaluation to Standard

Over the last year or so, I've been running my limited number of Windows Server instances using Windows Server Evaluation, letting me run Windows Server 2019 free for 180 days at a time, with a simple rearm to extend the free license for another 180 days (up to 5 times).

I was recently able to acquire a license key for Windows Server 2019 Standard and decided to do some research to see how difficult it would be to upgrade my Eval servers to Standard. Thankfully, the process is pretty painless and I will be walking you through it. In my case, I will be upgrading my primary domain controller.

Getting Started

To start, you'll want to open up powershell and run DISM /online /Get-TargetEditions. What this will do is spit out a bit of info letting you know what versions of Windows Server you can upgrade to.

Sidenote: It's worth mentioning that I've seen reports of Windows Server 2016 Eval (and prior) versions not allowing you to upgrade up from the Evaluation version.

Once you have confirmed that your target edition is available as an upgrade, you can begin the upgrade process by running the following command:

DISM /online /Set-Edition: /ProductKey:XXXXX-XXXXX-XXXXX-XXXXX-XXXXX /AcceptEula

For my purposes, I wanted to upgrade to ServerStandard, so I used:

DISM /Online /Set-Edition:ServerStandard /ProductKey:XXXXX-XXXXX-XXXXX-XXXXX-XXXXX /AcceptEula

Simply substitute the X's with your license key.

After running the command, you will be given the following output. Do not be alarmed if this process takes several minutes.

Once the process is complete, you will be prompted to reboot your server.

Post-Upgrade

After upgrading my server, I wanted to try my best to ensure all functionality was retained by domain controller. To do this, I visited my secondary domain controller and ran Test-ComputerSecureChannel. It's worth noting that this command needs to be run on a domain controller other than the one you just upgraded.

With everything working correctly, you should receive the True output depicted above.

Conclusion

That's all there is to it! I was pleasantly surprised that the upgrade only required 5 minutes of my time and a Standard license key.

Look forward to more guides in the near future. I intend to increase the frequency of my posts, documenting my learning related to a new job I started this week, which I will post about soon!