Microsoft has confirmed that a number of Windows Server 2019 and 2022 systems were “unexpectedly” upgraded to Windows Server 2025. This occurred on devices where updates were managed through third-party patch management tools. The company updated its Windows release health dashboard on November 6, indicating that Windows Server 2025 is now available as an optional update for organizations looking to perform an in-place upgrade.
In a statement released on Saturday, Microsoft clarified, “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.” They urged users to check their third-party update software configurations to ensure that feature updates are not deployed without consent, noting that the situation has since been mitigated.
This acknowledgment came after numerous reports from Windows administrators who discovered that their servers had been upgraded overnight to a version for which they did not possess a license. Microsoft explained that the optional update carried the “DeploymentAction=OptionalInstallation” tag, which should have indicated to patch management tools that it was not a mandatory update.
Microsoft blamed for “procedural error”
While not directly named, Heimdal, a company whose clients were impacted by this issue, attributed the upgrade complications to a “procedural error on Microsoft’s side, both with the speed of release and the classification” of updates. This information surfaced through communications seen by BleepingComputer and social media interactions involving Heimdal employees.
Unfortunately, by the time Heimdal managed to block KB5044284 across all server group policies, approximately 7% of their customers had already been upgraded to Windows Server 2025. A spokesperson for Heimdal was not immediately available for comment when approached by BleepingComputer.
Although Microsoft has stated that the known issue is mitigated, it has yet to provide guidance on how affected Windows administrators can revert the automatic upgrades, aside from restoring their systems from backups. A request for comment from Microsoft went unanswered when BleepingComputer reached out earlier today.
It is pertinent to mention that KB5044284 serves as a Patch Tuesday cumulative update for Windows 11 24H2 and, as of November, an optional update for Windows Server 2025. Microsoft has indicated that this situation will remain consistent, as “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.”
Additionally, Microsoft has resolved another issue where administrators were prompted to upgrade to Windows Server 2025 via a banner on the device’s Windows Update page under Settings. This message was intended for those seeking an in-place upgrade. However, many who proceeded with the installation found themselves needing to purchase a license to utilize the new version of Windows Server. Although a warning regarding the license requirement was displayed prior to the upgrade, numerous administrators expressed that the manner in which the update was offered was misleading, given the licensing stipulations involved.
