Upgrading Windows Server 2008 R2 to 2012 – via RDP

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!

Comments (8)

  1. Excellent, great for those who are migrating to 2012 !!

    Thanks !

  2. Raone Paulino says:

    Excellent, great for those who are migrating to 2012 !!

    Thanks !

  3. Brent Yager says:

    I'm going to try the RDP solution now.  The actual PC is only 100 feet away, but I'm lazy and want to see it work this way.  Will post my findings.

  4. wichets says:

    Excellent, great migrating to 2012 !!

    RDP Solution Work-fine.


  5. Scott Stauffer says:

    Trying this myself… It is in the room right next door, but headless and I am not a Domain Admin, so this is working… glad to hear that you had success too…

  6. tang samuel says:


  7. Anonymous says:

    My role has previously primarily focused on Microsoft Intune, nowadays it’s more towards our whole Enterprise

  8. Robert says:

    Didn’t work for me. Got the copying setup files screen and then it went back to the original install screen.