Buggy Windows Update starts automatically 'upgrading' Windows 2022 servers to Windows Server 2025

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The stuff of IT nightmares

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System administrators have taken to Reddit to report a bizzare situation where Windows Server 2022 systems are unexpectiedly being upgraded to Windows Server 2025. Fatboy40 reports on Reddit that this problem occured on a client's servers with no way to revert back to Windows Server 2022.

From the standpoint of a typical Windows user, upgrading from 2022 to 2025 might sound like a great idea, but this type of behavior can turn into a nightmare for system administrators/IT. Operating system upgrades for server-grade applications need to be vetted and tested by IT to insure that any software the associated business/enterprise software running on the new version of Windows doesn't break compatibility.

Windows 2022 Servers Unexpectedly Upgrading to 2025, Aaaargh! from r/sysadmin

Fatboy40 says that three days ago, all of their client's Windows 2022 servers had upgraded to Windows Server 2025 or "were about to do so." The cherry on top is that this update was being pushed despite the fact that Windows Server 2025 technically requires new licensing — since Windows Server 2025 is classified as an all-new version of Windows Server and not an update such as Windows 11 24H2.

But it seems that the update was accidentally classified by Microsoft as both an optional update and a security update for Windows Server 2022 machines, according to an employee from third-party update service Heimdal.

"Our team discovered this discrepancy in our patching repository," wrote Andrei from Heimdal via Reddit "as the GUID for the Windows Server 2025 upgrade does not match the usual entries for KB5044284 associated with Windows 11. This appears to be an error on Microsoft's side, affecting both the speed of release and the classification of the update. After cross-checking with Microsoft’s KB repository, we confirmed that the KB number indeed references Windows 11, not Windows Server 2025."

The worst part? This type of upgrade on Windows Server is technically not officially supported, unlike Windows 10 to Windows 11 upgrades. As a result, system administrators are stuck in the mud without any official method of downgrading their operating systems back to Windows Server 2022 if they don't have third-party solutions that offer system restore functionality from previously made backups.

Aaron Klotz
Aaron Klotz
Contributing Writer

Aaron Klotz is a contributing writer for Tom’s Hardware, covering news related to computer hardware such as CPUs, and graphics cards.

11 Comments Comment from the forums
  • DS426
    Wow. Free marketing for Linux!

    I didn't even know that Windows Server could in-place upgrade itself via Windows Update servicing.
    Reply
  • nrdwka
    DS426 said:
    Wow. Free marketing for Linux!

    I didn't even know that Windows Server could in-place upgrade itself via Windows Update servicing.
    Windows server is pretty much the same under the hood as normal windows, or ltsc, or iot. There is nothing what prevent to install windows server and use it as gaming pc (you will need to install additional components).
    Reply
  • RedRonin
    and no IT guy / management tought : Microsoft became a messed up update specialist, while i understand the updates needs, the update system must be blocked for at least 7-14 days, it gives time to see when Msoft messes up, anti virus okay but all os related, put a darn stop on them

    and if they haven't made an full os backup clone ....

    stupid thinking
    Reply
  • AtrociKitty
    This only happened automatically because of Heimdal. Windows Server 2025 appears as an optional upgrade you need to manually select from Windows Update otherwise. KB5044284 isn't pushed as a required update and will not install on its own under vanilla Server 2022.
    Reply
  • ohio_buckeye
    Good case for still running a wsus server so you can go in and decline that update.
    Reply
  • hotaru251
    how many yrs has MSFT been doing windows updates? Shouldn't have these type of issues with it :|
    Reply
  • adamXpeter
    Looks like these IT professionals learned nothing from the Crowdstrike scandal. Automatic update still turned on on a production server?
    Reply
  • jeremyj_83
    The worst part is Server 2025 just went GA on Nov 1st so there are a ton of bugs that still needs to be worked out.
    Reply
  • jeremyj_83
    ohio_buckeye said:
    Good case for still running a wsus server so you can go in and decline that update.
    Has WSUS gotten better over the last 5 years? When trying to run it on Server 2012 R2, it really sucked and never worked correctly.
    Reply
  • ex_bubblehead
    adamXpeter said:
    Looks like these IT professionals learned nothing from the Crowdstrike scandal. Automatic update still turned on on a production server?
    The biggest crime here is calling them "professional" ;)
    Reply