With the upcoming release of Windows Server 2022, many are going to be contemplating upgrading to the latest and greatest Microsoft Windows Server operating system. Some may have forgone the upgrade to Windows 2019, especially if they were already running Windows Server 2016. Also, what about legacy OS’es dating back to Windows Server 2008 R2? What is the upgrade path from Windows Server 2008 R2 to Windows Server 2022? In this post, we will take a look at the in-place upgrade Windows Server 2008 R2 to Windows Server 2022. Has this changed from previous jumps to Windows Server 2019? Show Multiple upgrade stepsOne thing is for sure. Don’t expect to be able to stick the Windows Server 2022 ISO into a Windows Server 2008 R2 server, click upgrade, and then after a few reboots have a Windows Server 2022 server upgraded from Windows Server 2008 R2. In the following lab walkthrough, I am taking a clean Windows Server 2008 R2 installation all the way up to Windows Server 2022. In the following graphic taken from the Techcommunity blog post, you see the steps and support detailed at the time of that writing for taking a Windows Server 2008 R2 server to Windows Server 2019. With that installation, there is only two steps: 
So with this process, I will be trying the following:
In case, like me, you are wondering if Microsoft pulled off some magic with Windows Server 2022 and we would be able to go straight to 2022 from 2008, I tried this. As expected, the option is greyed out to keep files, settings, and apps when you try to go from Windows Server 2008 R2 directly to Windows Server 2022.
So to reiterate, the process you will need to follow is to upgrade your Windows Server 2008 R2 server to Windows Server 2012 R2. Then, you will mount the media for Windows Server 2022 and upgrade Windows Server 2012 R2 to Windows Server 2022. In-Place Upgrade Windows Server 2008 R2 to Windows Server 2012 R2For the most part, the screens below are probably screens you have seen in the past if you have performed an in-place upgrade to Windows Server 2012 R2. However, for posterity, I have attached the screenshots below. After the clean installation of Windows Server 2008 R2 in the lab environment, I mounted the media for Windows Server 2012 R2 for performing the in-place upgrade to Windows Server 2012 R2. Click the Install now button. There are a few options here you can choose. You can go online and install updates as well as help to make the Windows installation better (option). Next, you will need to provide a license key for the Windows Server 2012 R2 installation. After you enter the license key, click Next. Be sure here on the next screen to choose GUI if you want to have a GUI. It doesn’t default to GUI if you are coming from a GUI version of 2008 R2, so make sure to select the appropriate option here. EULA. Next, pay attention to the option you choose on the Which type of installation do you want? screen. For an upgrade, you want to select Upgrade: Install Windows and keep files, settings, and applications. Otherwise, you will be performing a clean server installation that will erase your data. The upgrade installer will present a warning of sorts on the Compatibility report. Basically, it states you need to verify compatibility with your applications on Windows Server 2012 R2 since this is the destination after the upgrade process finishes. Once you click Next, the upgrade process begins. You will see your server reboot several times during the process. Below, the process is almost complete. It is finishing up the process before completing. After a final reboot, the server will boot to the very familiar Windows Server 2012 R2 login screen. In-Place Upgrade from Windows Server 2012 R2 to Windows Server 2022The final leg of the journey is to take the Windows Server 2012 R2 server to Windows Server 2022. The process is the same for this portion of the upgrade. Simply mount the Windows Server 2022 media and run the installer. As a note, I am using the Windows Server 2022 Preview media and this worked just fine. Enter your product key. The product key below is the publicly available key that is documented here: KMS client setup keys | Microsoft Docs Again, pay attention to what you select here. (Desktop Experience) equates to GUI. EULA. On the Choose what to keep screen, choose the Keep files, settings, and apps. After a moment, the installer will be Ready to install. Click Install. You will see Installing Windows Server progress. After a while, the screens will change a few times with the progress indicator moving forward. In just a short amount of time, I had the Windows Server 2022 login screen displaying. Of course, I had no data really or any applications installed. Verifying the Windows Server version is Windows Server 2022. Video of the in-place upgrade process from Windows Server 2008 R2 to Windows Server 2022In-place upgrade from Windows Server 2008 R2 to Windows Server 2022 video ConcludingHopefully, this quick walkthrough to validate the process to go from Windows Server 2008 R2 to Windows Server 2022 will shortcut the information gathering process to get legacy servers updated to Windows Server 2022. I was hoping Microsoft had pulled out all the stops with Windows Server 2022 and it just work from even the legacy server versions, but realistically, the process is the same as it has been for getting to 2019. So, if you have an old legacy Windows Server 2008 R2 server that you want to take all the way to 2022, you will have two different upgrade processes: one from 2008 R2 to 2012 R2, and the other from 2012 R2 to 2022. |
