In order to save some fuel/time/energy I’m upgrading one or our test servers from Windows Server 2008 R2 to Windows Server 2012 via RDP. Not recommended or supported in any scenario <insert disclaimer here>.

Before you start, make sure all Virtual Machines are in a OFF state, setup wont be possible if they are set to SAVED or RUNNING.

 

Here we go!

Start a RDP session, I decided to take the Admin session:

 

Check the version currently installed:

Download and extract the ISO of the new Operating System:

Start the installer

Following the wizard:

- Download the latest updates for setup.

- Enter a valid product key (you can even ALT-TAB to copy it from somewhere)

- Choose a Windows Edition (with or without a GUI).

- Decide whether you accept the License Terms or not.

- Choose to upgrade.

And now… we wait…

After a while (and some reboots) the server responds to ping request again:

It took some more coffee until I could reach the server using RDP again.

Install the latest updates and: upgrade finished!