Several users have reported that their Windows Server 2022 systems are being automatically upgraded to Windows Server 2025 without having the necessary licenses. This problem seems to be associated with an API error.
Windows Server 2025 is now accessible for all, and while it’s an optional update like other significant releases, some users have observed that their Windows Server 2022 installations are upgrading to Windows Server 2025 unexpectedly overnight. Instead of a forced installation from Microsoft, it appears that an alternative issue is at play.
On November 5, small businesses utilizing third-party patch management tools (designed for handling security and feature updates for servers) reported that their systems had automatically transitioned to Server 2025. This poses a significant concern, as opposed to Windows Updates, Windows Server versions are not complimentary and necessitate distinct licensing.
An affected user shared, “All of our Windows 2022 Servers had either upgraded themselves to 2025 overnight or were on the brink of doing so. This came as a surprise because we are not prepared to make that leap for various reasons, and the necessary licensing is not in place.”
It seems that Microsoft may have made an error in the labeling of updates on its API, leading third-party tools to mistakenly identify Windows Server as a security update. Reports indicate that the underlying issue stems from Microsoft erroneously categorizing the Windows Server 2025 upgrade (KB5044284) as a security update in the Windows Update API.
This mislabeling led third-party patch management solutions, such as Heimdal, to flag it as a critical security update that needed immediate installation.
Consequently, tools relying on the API will automatically download and install the update on Windows Server 2022 systems, unexpectedly transitioning those systems to Windows Server 2025.
The unplanned upgrade, carried out without appropriate licensing for the new version, has resulted in complications, including the occurrence of unlicensed servers.
In October, Microsoft released an update KB5044284 for Windows 11 24H2, intended as a security release. However, there was a mix-up on Microsoft’s end, resulting in the update being misclassified and inadvertently providing an upgrade route to Windows Server 2025 via the API.
Although the API is not commonly utilized directly by businesses, those using third-party tools that depend on APIs might encounter this problem.
What potential issues could arise from this situation?
A Reddit post indicated that patch management firm Heimdal is aware of the feedback and attributes the issue to the misclassification by Microsoft in the Windows Update API.
Heimdal has confirmed that it has intervened to block the KB5044284 update to avert unintended upgrades to Windows Server 2025.
“On November 5th at 12:16 UTC, Heimdal received a notification from a customer regarding unplanned upgrades connected to Windows Server 2025 in their system. Given the initially limited impact, pinpointing the root cause required some time. By 18:05 UTC, we identified the problem as stemming from the Windows Update API, where Microsoft had incorrectly categorized the Windows Server 2025 upgrade as KB5044284,” the company explained in a statement.
For those impacted, companies now face decisions on whether to restore their servers from backups, rebuild them, or acquire new licenses for Windows Server 2025.
Other organizations that depend on APIs and third-party tools might also experience similar problems with the auto-installation of Windows Server 2025. Some users have reported that the update presented itself as an optional feature, while others saw it installed automatically in accordance with their update policies.
About The Author
Mayank Parmar is an entrepreneur who established Windows Latest. He serves as the Editor-in-Chief and has contributed to various subjects throughout his seven-year career, but he is particularly recognized for his thorough analysis of Microsoft’s Windows. His articles and research have been cited by numerous esteemed platforms including CNN, Business Insider, Forbes, Fortune, and CBS Interactive, as well as Microsoft and many others over the years.