Navigating Windows Update Side Effects: Troubleshooting Connection Errors with Windows 365

Microsoft’s January Patch Day presented a new set of challenges for users, as the latest security updates for Windows have led to significant connection issues with Windows 365 and Azure Virtual Desktop. Following the distribution of these updates, Microsoft reported problems regarding credential prompt failures that prevent users from signing in through the Remote Desktop application on Windows client devices.

The problems are affecting various Windows builds including Windows 11 versions 25H2, 24H2, and 23H2, as well as Windows 10 versions 22H2 and 21H2, and several Windows Server editions. The implications of these issues were detailed by Microsoft in an entry added to their Windows Release Health Center, indicating ongoing investigations to solve these issues.

To mitigate the impact on users, Microsoft has provided two temporary workarounds. Firstly, users can switch to using the Remote Desktop client for Windows, which is available for download on a dedicated Microsoft webpage. Additionally, they can access the Windows app through a web client provided on windows.cloud.microsoft, which is not currently expected to experience these connection problems.

This situation arose shortly after the January Patch Day, during which Microsoft also addressed an already exploited vulnerability (CVE-2026-20805). The resolution of these security updates is essential for maintaining system integrity and user security across multiple Windows platforms.

For ongoing updates and further assistance, users are encouraged to monitor Microsoft’s official channels.


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