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January 15, 2026

Troubleshooting Connection Errors with Windows 365 After Recent Windows Update

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Microsoft’s January Patch Day updates have led to unexpected connection issues with Windows 365 and Azure Virtual Desktop. Following the distribution of these security updates, the company warned users about credential prompt failures occurring during Remote Desktop connections using the Windows app.

Details of the Connection Issues

According to Microsoft, affected users may experience sign-in failures on specific Windows versions, which include Windows 11 (versions 25H2, 24H2, 23H2), Windows 10 (versions 22H2, 21H2), and several Windows Server editions (2019, 2022, 2025). The issue has been documented in the Windows Release Health Center, where Microsoft confirmed they are actively investigating and troubleshooting the problem.

Temporary Solutions Offered

For users affected by these issues, Microsoft has proposed two temporary workarounds:

  1. Switch to the Remote Desktop client for Windows to connect to Azure Virtual Desktop. Users can find the download and version history on Microsoft’s website.
  2. Utilize the Windows app available as a web client through windows.cloud.microsoft which is reportedly free from these connection issues.

Context of January Patch Day

The updates released during the January Patch Day not only included security enhancements but also addressed previously exploited vulnerabilities, specifically CVE-2026-20805. These updates highlight the complexities and occasional drawbacks that can accompany routine maintenance and security improvements in widely used operating systems.

For those experiencing difficulties, it’s recommended to monitor the Microsoft January Patch Day updates for further advice and ongoing solutions.


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