In-Place Upgrade Windows Server 2008 R2 to Windows Server 2022

 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?

Multiple upgrade steps

One 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:

Windows server 2008 r2 in place upgrade to windows server 2019

• Upgrade Windows Server 2008 R2 to Windows Server 2012 R2
• Upgrade Windows Server 2012 R2 to Windows Server 2019

So with this process, I will be trying the following:

• Upgrade Windows Server 2008 R2 to Windows Server 2012 R2
• Upgrade Windows Server 2012 R2 to Windows Server 2022

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.

Keep files settings and apps greyed out directly from windows server 2008 to 2022

In-Place Upgrade Windows Server 2008 R2 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 R2

For 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.

Launching the in place upgrade to windows server 2012 r2

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).

Get important updates during the in place upgrade

Next, you will need to provide a license key for the Windows Server 2012 R2 installation. After you enter the license key, click Next.

Enter the windows server 2012 r2 product key for the in place upgrade

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.

Choosing the windows server 2012 r2 operating system version

EULA.

Accept the windows server 2012 r2 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.

Choose the upgrade installation of windows server 2012 r2

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.

Compatibility report upgrading from 2008 r2 to 2012 r2

Once you click Next, the upgrade process begins.

Upgrade process from windows server 2008 r2 to windows server 2012 r2 begins

You will see your server reboot several times during the process.

Windows server will reboot a few times during the upgrade to 2012 r2

Below, the process is almost complete. It is finishing up the process before completing.

Upgrading to windows server 2012 r2 nearing completion

After a final reboot, the server will boot to the very familiar Windows Server 2012 R2 login screen.

Upgrade to windows server 2012 r2 completes successfully

In-Place Upgrade from Windows Server 2012 R2 to Windows Server 2022

The 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.

Beginning the process to upgrade windows server 2012 r2 to windows server 2022

Enter your product key. The product key below is the publicly available key that is documented here: KMS client setup keys | Microsoft Docs

Enter the product key for windows server 2022

Again, pay attention to what you select here. (Desktop Experience) equates to GUI.

Select the windows server 2022 image you want to install

EULA.

Accepting the eula for the windows server 2022 upgrade

On the Choose what to keep screen, choose the Keep files, settings, and apps.

Choose the applications and data you want to keep

After a moment, the installer will be Ready to install. Click Install.

Ready to begin the upgrade to windows server 2022 from windows server 2012 r2

You will see Installing Windows Server progress.

Windows server 2022 begins installing

After a while, the screens will change a few times with the progress indicator moving forward.

Working on updates and other processes complete during the upgrade to windows server 2022

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.

Windows server 2022 login screen after the upgrade completes successfully

Verifying the Windows Server version is Windows Server 2022.

Verifying the windows server version after the upgrade

Concluding

Hopefully, 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.