Windows 2022 Servers Unexpectedly Upgrading to 2025

(old.reddit.com)

91 points | by nielsole 2 days ago ago

46 comments

  • thro1 a day ago

    > Microsoft appear to class this as a "Security Update",

    >> 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

    Shall Microsoft now provide the missing license ?

  • drw85 a day ago

    This once again highlights how bad the ecosystem with 3rd party tools used for basic system maintenance in the MS environment is. And how much companies and admins rely/depend on those.

    I don't really understand why there are so many commercial third party tools being used to do basic things. But they cost a good amount of money and cause a lot of problems.

    • zuhsetaqi a day ago

      In this case at least it was Microsofts fault

      • thro1 a day ago

        Yes. For automation software it's fully updated (not: upgraded) target system definition.

      • thrw42A8N a day ago

        No, it wasn't. This failure happened at the side of the user - their central policy configuration or so. Microsoft pushed the update correctly.

        • superb_dev 18 hours ago

          Did we read the same article? Microsoft labeled an update as "security updates" when it was in fact an upgrade to Windows Server 2025

          • lostmsu 17 hours ago

            Did they say they wouldn't?

            In the absence of Heimdall 2022 Server doesn't install it along with other security updates.

            • superb_dev 16 hours ago

              Wouldn't what?

              Also given other peoples experiences in this comment section, that doesn't seem to be true.

              • lostmsu 11 hours ago

                I can't find anyone without Heimdall who would claim it happened to them. For all we know this is 100% Heimdall bug.

        • Brian_K_White a day ago

          It sounds like the 3rd party tool did what MS told it to do.

          • thrw42A8N a day ago

            Nope, my servers are just fine.

        • a day ago
          [deleted]
    • heraldgeezer 18 hours ago

      This would happen if you just let Windows Update do its thing. As is fine on client machines usually for security.

      On Azure it is the default even https://imgur.com/a/RvEx3yn

  • gary_0 a day ago

    Nobody ever got fired for running a Linux server...

    • taskforcegemini a day ago

      not the phrase I'd use to make that argument

    • doublerabbit a day ago

      I accidentally deleted /etc/ thanks to a syntax error in my script and got fired.

      I hated the boss of DevOps team and they hated me. Greatest thing to ever happen to me.

      • teruakohatu 18 hours ago

        Firing someone for a mistake they will have learnt never to make again is not just pointless but also counterproductive.

        • doublerabbit 7 hours ago

          It was more he had a grudge of his because I would always push back his ideas. This made it a hostile environment as I always had to ensure I cover my arse in all area's. This was his "gotcha!" moment.

          He wanted to put me on-call with no pay increase, wanted eight Cassandra servers for no reason. All this other crap because he had herd buzz words.

          They were trying to brown nose the position of the CTO as at the time the company had none.

          Shiite company that collapsed six months later.

      • ASalazarMX a day ago

        Root comment still stands up, unless you were the one running the Linux server.

        • doublerabbit 7 hours ago

          I was. My install, my setup. Linux Engineer was my job. We are talking about 15-20 developers all using pirated Windows 10 for workstations.

      • 19 hours ago
        [deleted]
      • 6510 a day ago

        I've always wondered what etc refers to.

  • m463 18 hours ago

    I wouldn't be surprised if it "upgraded" all your data into azure and disabled local admin...

  • jeroenhd a day ago

    Looks like this is an issue with a a third party update client being confused by a potential misclassification in Microsoft's side about the update (security update vs upgrade).

    What I'm most surprised by myself is that there doesn't seem to be an option to revert this according to the comments. I'm pretty sure consumer Windows allows downgrades for upgrades installed in this manner, I can't imagine the pain it'd be to need to manually undo all the damage after an unintended upgrade using automated tooling!

    • graemep a day ago

      What do third party update clients do? Why are they used? Why are they even able to upgrade the OS version?

      Not a Windows version and unfamiliar with how it works.

      • worewood 18 hours ago

        Probably the third-party solution offers functionality not available from Microsoft, for example integrating with other management software they may have, enabling automated blue-green scheme for applying updates, so they can accurately measure the impact of updates for example.

    • tallanvor a day ago

      I agree that this looks like a 3rd party issue. They claimed that KB5044284 was the update, but others have noted that after installing that update, they had the option to upgrade to 2025 but it didn't happen automatically - seems the 3rd party RMM somehow pushed a command to start the upgrade.

      Honestly, I guess since it's an SMB it might make sense that they aren't able to test all patches before applying them in production, but you'd hope they'd delay the installation for a few days to let others catch major issues.

  • lousken 18 hours ago

    thank god i moved my entire company to debian last year it's enough to deal with w11 on its own

  • Habgdnv a day ago

    <sarcasm>

    A similar thing happened to me last month. My Ubuntu server suddenly started showing a countdown, warning that my firewall was blocking Canonical's ‘essential data’ pings and threatened to revoke my apt privileges. I gave it a pass-through, but the next day, it upgraded itself to Ubuntu Galactic Cosmic and replaced all my bash scripts with PowerShell. Still getting used to the mandatory Snap packages for 'ls' and 'cat' now…

    </sarcasm>

    • 6510 a day ago

      Have you tried switching it off and leaving it off?

  • kencausey a day ago

    An offer to update to Server 2025 is showing up in Windows Update for a Server 2019 system to which I have access but it is not auto-installing.

    • a day ago
      [deleted]
    • hulitu 8 hours ago

      > but it is not auto-installing.

      for now. /s

  • dijit a day ago

    well thats terrifying.

    It would be a good horror story for halloween, but that was last week…

  • orionblastar 2 days ago

    This seems to be used by Microsoft like the Windows 7 and 8.1 to Windows 10 upgrades.

    • drooopy a day ago

      It gives me chills thinking of production servers being magically upgraded to a new and untested version of Windows.

      • more_corn 16 hours ago

        It gives me chills thinking of production servers running windows.

      • blibble a day ago

        but it's the most stable and secure version of Windows yet

        • ASalazarMX a day ago

          I have the most stable and secure version of Windows in my personal laptop, perfectly safe sleeping in its partition until I boot it every few months to install updates.

    • Mountain_Skies 2 days ago

      Sure, for home versions but updating a server version without explicit direction to do so is really bad for business.

      • grujicd a day ago

        In this case, based on comments there, new server is not licensed anymore and not activated after the upgrade. Making this problem much worse, as options are either purchasing new licenses or reinstalling everything.

        Edit: it's not clear to me how much responsibility lies with 3rd party update management tool and how much with Microsoft. This update doesn't seem to automatically run by itself, but it might be misclassified so that these tools think it's a security update and just deploy like any other patch.

      • hulitu 8 hours ago

        For your business. Not for Microsoft's

  • jaimsam 15 hours ago

    Yet another thing that does not exist in a sane OS. Oh, if only Bill Gates hadn't done his dirty deeds.