Servers getting upgraded to 2025?

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Be aware, I’m seeing reports on reddit here and here that KB5044284 is being offered up to Server 2019, 2022 and is upgrading them to Server 2025. As
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Susan Bradley Patch Lady/Prudent patcher

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abbodi86, mcbsys, Casey S

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Which also explains this image I’ve seen on social media.

Susan Bradley Patch Lady/Prudent patcher

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mcbsys

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Thanks Susan!

Our team has blocked that KB now across our entire org.  Some notes:

Unless you have a current Software Assurance subscription along with your correctly scaled Server 2022/2019 license core count, accepting this update WILL put you into non-compliance with your license unless you purchase new Server 2025 licenses.

In place upgrades have become drastically more reliable since the 2016 days, but there are some gotcha’s that our team has identified:

Domain controllers should be migrated to new builds, not upgraded in place.  MS technically supports upgrading DC’s with some special and convoluted instructions, but it has not proven reliable for our team.

Application servers, including SQL servers, generally upgrade in place just fine, but many LOB applications will trigger a re-activation workflow.  You may also need to re-apply all prerequisite packages like .Net and other third party code libraries.  Be prepared and make sure your software is on a current and supported license, that the applications re-activation is possible (you have a working key), and that the system requirements for your application include the new server OS as a supported platform.  If any of those checks are not in place, defer the upgrade.

Dedicated file servers generally are safe to upgrade in place.

Internal Certificate Authority server roles don’t play nice with upgrades in place, migrate the role to a new server (often on a DC.)

Radius Servers have also not played as nice as we would like, recommending migrating to a new server.

ALWAYS do a test upgrade in a sandbox with the roles and applications your business uses!  Document every workaround you make during the test so you can replicate that on production.

And finally:  Make sure you have a fully restorable backup image, refreshed just before the upgrade, ready to use if you need to rollback!

Never -ever- upgrade a server without a known good recent backup.

Cheers!

~ Group "Weekend" ~

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Well that would be a nasty surprise. @AndrewMRQuinn posted a follow-up early this morning. It looks like MS has removed 2025 as an optional update, at least for now. I checked for updates today on a 2022 machine and no upgrade was offered.

https://x.com/AndrewMRQuinn/status/1854457797699686671

Has there ever been an update ever offered through Windows Update, on any OS, that was a chargeable event, i.e. one that breaks your current license? I am certainly conditioned to expect patches on the Windows Updates screen to be free.

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Every things must have a first

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Microsoft is just sloppy anymore. Too obsessed with the wrong things, and cannot seem to properly review and double check anything. I mean 24H2 is a dreadful mess too and should have stayed in beta a lot longer. So does Microsoft deliberately push these updates out into public hoping for more beta testers?

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it’s still in the catalog, and same file size as the one for Windows 11.

https://catalog.update.microsoft.com/Search.aspx?q=KB5044284

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Windows Server 2025 known issues and notifications | Microsoft Learn
Someone else please read this information carefully and see if they are saying they intend to continue the same behavior as it seems to say?

November 2024
Windows Server 2022 and Server 2019 unexpectedly upgraded to Windows Server 2025
Status Originating update History
Mitigated N/A
Last updated: 2024-11-09, 12:38 PT
Opened: 2024-11-09, 12:16 PT
Windows Server 2025 is intended to be offered as an Optional upgrade in Windows Update settings for devices running Windows Server 2019 and Windows Server 2022. Two scenarios were observed in certain environments:

• Some devices upgraded automatically to Windows Server 2025 (KB5044284). This was observed in environments that use third-party products to manage the update of clients and servers. Please verify whether third-party update software in your environment is configured not to deploy feature updates. This scenario has been mitigated.
• An upgrade to Windows Server 2025 was offered via a message in a banner displayed on the device’s Windows Update page, under Settings. This message is intended for organizations that want to execute an in-place upgrade. This scenario has already been resolved.

The Windows Server 2025 feature update was released as an Optional update under the Upgrade Classification: “DeploymentAction=OptionalInstallation”. Feature update metadata must be interpreted as Optional and not Recommended by patch management tools.

We advise organizations to use Microsoft-recommended methods to deploy Windows Server feature updates.

Next steps: Microsoft is working with third-party providers to streamline best practices and recommended procedures. The visibility of the feature update offer banner can be controlled by setting the target version to “hold” in the Group Policy “Select the target Feature Update version”. We will update this documentation in the coming days with additional information about this group policy once it is available.

Note: The Windows Server 2025 feature update was made generally available on November 1, 2024, as KB5044284, which was the same KB number used for Windows 11, version 24H2. This was the KB numbering for both these client and server Windows updates available at that time. Future updates released for Windows Server 2025 and Windows 11, version 24H2 will share the same KB numbers, but will have different release note sites and links.

https://learn.microsoft.com/en-us/windows/release-health/status-windows-server-2025

Moderator’s Note: Cleaned up a lot of HTML that made the post nearly unreadable. Use the Text tab to paste from web pages.

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mcbsys

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Server 2025 updates will be always the same as Windows 11 24H2 x64

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