[German]It's a strange information about Windows Server 2025 reported to me by German blog readers. Readers were offered an upgrade to Windows Server 2025 under Windows Server 2022 (and Windows Server 2019) for download and installation via Windows Update. It is currently unclear whether this is a mistake or a deliberate offer. In any case, the problem is that users do not have a license for Windows Server 2025 and are therefore falling into a trap with the upgrade offer.
Update to Windows Server 2025 offered
There is quite an oddity mentioned by several German blog readers: It looks like administrators on Windows Server 2022 (and Server 2019) are being offered to upgrade to Windows Server 2025. Two blog readers have sent me corresponding screenshots.
The above screenshot comes from a German reader and shows that the download and installation of Windows Server 2025 is offered there in Windows Update. Gerrit also wrote that he had received a screenshot from a customer, according to which he can upgrade his Windows Server 2022 to Windows Server 2025 via Windows Update.
The reader wrote that he was unable to reproduce this on any of his systems. He also found nothing about this offer on the web. However, I have received two independent reader reports with such screenshots.
More user reports
Two other German blog readers have pointed out this upgrade trap in the discussion area of my blog. One reader refers to this reddit.com thread, where the problem is already being discussed.
Update KB5044284 as root cause?
In the reddit.com thread, the affected person writes that Microsoft has classified the update KB5044284 from October 8, 2024 as a security update. The Heimdal patch management tool used classifies the update internally as an upgrade and also displays "Update Name: Windows Server 2025".
It is therefore possible that this KB is being misclassified by Microsoft and/or third-party patch management tools, but this needs to be investigated further. However, I can't really grasp this information. Patchmanagement.org also lists this update as being responsible.
Another reader report and additions
A second blog reader reports in the discussion area that he was also offered the upgrade under Windows Update to Windows Server 2022 21H2 Datacenter on 05.11.2024. There it says:
Windows Server 2025
The next version of Windows with new features and security improvements is available. Select "Download and install" and the upgrade will begin after other updates in your queue have been completed. Your device may need to be restarted.
[Download and install]
As the user wrote: "One click away from disaster. Handy if you want to/can do that. Unfortunately there is no mention of possible cost consequences if the CALs no longer fit. I have not yet found the GPO settings or regkeys to make this offer disappear. Dear friends in Redmond – we want and need to keep control of our systems, whether it slows down your business or not!"
German blog reader Johnny has informed me that the update is not as bad as described above. Before the installation, the above dialog box appears with a note about the consequences and that a license key is required.
The comments to my German blog post indicate that this upgrade offer is not only available for Windows Server 2022 but also for Windows Server 2019. An upgrade option is ok, but why this is automatically offered via Windows Update is not clear to me..
Microsoft offers upgrade technically
However, Microsoft has described in this support document that an upgrade from an older Windows Server version is possible from Windows Server 2025.
The above screenshot reflects this technical situation. At this point the question arises, what about the required license? Has Microsoft made a mistake or has something been changed in the Software Assurance contracts so that the upgrade would be covered by the licenses?
