Microsoft has successfully resolved a persistent issue that led to unexpected upgrades for systems operating on Windows Server 2019 and 2022, which were inadvertently elevated to Windows Server 2025. This situation first came to light in September 2024, when numerous Windows administrators reported that their servers had been automatically upgraded overnight to a version for which they lacked the necessary licenses.
Initially, Microsoft indicated that organizations seeking to perform in-place upgrades were presented with an upgrade option for Windows Server 2025 through a notification banner within the Windows Update settings. However, the company attributed the problem to third-party update management software that had not been configured correctly. In response, software developers contended that the upgrade issues stemmed from a procedural misstep on Microsoft’s part, particularly concerning the release speed and classification of the updates.
When BleepingComputer reached out for clarification on the root cause of these automated upgrades, Microsoft did not provide an immediate response. However, this week marked a turning point, as the tech giant announced that the issue has been rectified, allowing customers to once again check for upgrades via the Settings app.
Updates and Fixes
In a recent Windows release health update, Microsoft confirmed, “This issue is resolved and Microsoft has re-enabled the upgrade offer via the Windows Update settings panel.” For those interested in further details regarding the feature update process, Microsoft directed users to their learning resources, specifically the section on performing in-place upgrades of Windows Server.
Last month, Microsoft also released an out-of-band update aimed at addressing issues with the March 2026 non-security preview update, which had been retracted due to installation complications. Just days prior, an emergency update was deployed to fix a significant problem that arose from the March Patch Tuesday security updates, which disrupted sign-ins across various Microsoft applications, including Edge, Teams, OneDrive, and Microsoft 365 Copilot.
Additionally, two other out-of-band updates were rolled out last month to tackle a Bluetooth device visibility issue and to patch several security vulnerabilities within the Routing and Remote Access Service (RRAS) management tool, particularly affecting Windows 11 Enterprise devices.
As Microsoft continues to navigate these challenges, the focus remains on ensuring that their systems operate smoothly and securely for all users.
