How to Upgrade from Windows Server 2019 Core to Windows Server 2022 Core

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Continuing my mini-series on providing IT Pros valuable assistance and guides moving their workloads, roles, and Server-based applications to Windows Server 2022, here is my guide to upgrading, in-place, from Windows Server 2019 ‘Core’ to Windows Server 2022 ‘Core.’ Thankfully, the overall setup routine is similar to using the GUI (Desktop Experience) in Windows Server. But, there are some nuances and a few extra steps. Let’s get to it!

Quick Background – What is ‘Core’?

Now, now. Microsoft would be very disappointed if they heard some IT Pros asking what the ‘Core’ installation of Windows Server is and what it’s used for – the Core installation option is the recommended option. Why? Largely for security purposes and a more nimble, efficient installation base. Being able to manage servers remotely is efficient, and oftentimes, easier. Remote management tools, like Windows Admin Center, make it very simple to monitor, manage, and perform all server-related tasks. Excluding the GUI offers a more robust and safe environment, harder for hackers to exploit.

Because the vast majority of the GUI, or the Desktop Experience, is not installed, the footprint is much smaller. The fundamental structure of the O/S affords a smaller attack vector. There is no ‘explorer.exe’ to hack or exploit. There is a command-line and a limited graphical footprint. When you see the Windows Setup screens below, it looks, well, let’s be honest – not so elegant…that’s because the rich GUI development arena is missing. The engineering and development teams simulate a GUI as best they can. It’s similar to how developers sprinkled ASCII characters on your monochrome command-line only monitors to ‘draw’ things on your screen.

To manage these Core servers, you can run commands at the command line, run PowerShell cmdlets natively in the shell, or use other GUI remote management tools from other systems, like Windows Admin Center, Computer Management, and other MMC-based tools (DHCP, DNS, WSUS, IIS, etc.). For all you WAC (Windows Admin Center) fans, I’ll write up a post on this very helpful, and constantly updated tool in the coming weeks!

Upgrade Steps Outlined

If you read my article on upgrading from Windows Server 2012 R2 to Windows Server 2022, you saw the initial steps to copy the ISO for Windows Server 2022 to the desktop, right-click on it, choose Mount, and then run setup.exe. But, there is no desktop. Only this shell…

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Now what? Well, the ‘workaround’ for this missing GUI element is to mount the ISO directly to your server. If you’re using Hyper-V or VMWare, just mount the ISO for Windows Server 2022 as the server’s DVD Drive. If you’re using a physical server, insert your USB stick with the installation media in the server, or use iDrac or CIMC remote tools to virtually mount the ISO. Then, choose option (15) to ‘Exit to Command Line’, and, at the command line, type:

D: (or whichever drive letter your ISO is mounted to)



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Eeek. See? Not too lovely, but it gets the job done, right? No worries. Now, click Next!

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Click Next.
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Again, as of this writing, there are no valid VLKs (Volume License Keys) available yet. When they are, you would optionally be able to enter them here. Also, at this point in Setup, there should eventually be a link at the bottom that says ‘I don’t have a product key’, or something similar. Later after the setup is complete, you would be able to enter a key and Activate Windows. Again, this is coming soon.
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So here, we will leave the default option. If Core is installed, Windows Setup will assume you want to keep it the same. We could go from Core to Desktop Experience, but, let’s keep things simple at the moment. After clicking Next…,

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The biggest convenience feature of an in-place upgrade is the seamless experience going from A -> B. You don’t need to copy your files elsewhere or worry (essentially) about re-installing any applications. They will be retained. Note: ALWAYS back up the state of your server before performing any upgrades! Click Next. (If you want to wipe the slate clean, choose ‘Nothing’ above and all non-system files will be removed during Setup.

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We are all set to install Windows Server 2022! Click Install.

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When Setup is done, you will be back at your server, ready to login.

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Conclusion – Next Steps!

That is it! Easy as cake. Pie! Easy as pie! After logging in, you’ll notice that Microsoft has made the launching of ‘SConfig’ automatic. You just need to run this PowerShell command if you would rather the server boots to the PowerShell prompt, not SConfig.

Set-SConfig -AutoLaunch $false
At this point, you can begin your application testing, validation, and finish all your standard post-setup tasks. Once you have your Volume License Key, you can run these commands at the shell to enter the key and activate Windows:
slmgr.vbs /ato
Coming up – more upgrades and installations to Windows Server 2022. If you have any specific scenarios you’d like me to highlight or pursue, please leave a comment!

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