Fixing SSH Issues on Windows 11: Workarounds and Updates

Windows 11 users relying on remote SSH connections may have noticed a sudden hiccup in their workflows. A recurring bug has disrupted SSH operations on certain Windows 11 systems—particularly affecting the 22H2 and 23H2 versions. Fortunately, Microsoft is already on the case, testing a permanent solution that should be rolled out in a future cumulative update. Until then, a temporary workaround is available for affected users.

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Overview of the Issue​

In recent reports, including an article by Ruetir, it was detailed that SSH—an essential tool for remote management and secure communications—suddenly stops working on certain Windows 11 devices. The issue appears linked to some cumulative security patches, most notably updates KB5044285 and KB5044380 from October 2024. While the initial glitches were detected in Windows 11 Enterprise and Education editions, the fault has now been observed on Home and Pro editions too.
In simple terms, when attempting to establish remote connections via SSH, users may encounter errors due to a failure of the OpenSSH service to start. Microsoft has acknowledged the problem and is actively testing a fix to restore reliable SSH connectivity.

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What’s Causing the Disruption?​

Cumulative Updates and Unexpected Side Effects​

Security updates are meant to protect your system from vulnerabilities, but sometimes enhanced protections can inadvertently interfere with system functionalities. In this case, the October 2024 security patches introduced changes in how certain system directories handle permissions, which in turn caused the SSH service to fail on startup. The affected directories include:

• C:/ProgramData/ssh
• C:/ProgramData/ssh/logs

These folders house critical configuration files and logs for OpenSSH. Misconfigured permissions within these directories can prevent the SSH daemon from accessing necessary files, halting remote connections.

Who Is Affected?​

• Enterprise and Education Editions: Initially, the problem was spotted here.
• Home and Pro Editions: Following the updates, these consumer versions have reported similar issues.
• Selective Device Impact: Not every Windows 11 installation shows the issue. The bug appears to affect a subset of devices running the specific cumulative updates mentioned above.

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Microsoft’s Response and the Road Ahead​

Microsoft has swiftly acknowledged the SSH connection issue. The tech giant is actively working on a comprehensive solution that — once finalized — will be distributed as part of a cumulative patch. This update, expected to roll out in the coming weeks, aims to permanently resolve the permission conflicts causing the SSH service woes.

Why a Permanent Fix Is Crucial​

• Remote Administration: For IT professionals and system administrators, reliable SSH connectivity is vital for managing servers and remote environments.
• Security Compliance: Many remote workflows depend on the secure tunneling that SSH provides. A broken connection can lead to increased vulnerabilities or a lapse in remote monitoring.
• User Trust: Continuous issues like these, even when temporary, challenge user confidence. Microsoft’s proactive approach to fix the problem reaffirms its commitment to stability in Windows 11 updates.

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Temporary Workaround: Adjusting File Permissions​

While waiting for the definitive patch, Microsoft recommends a temporary solution: manually updating the ACL (Access Control List) permissions of the affected directories. This workaround re-establishes the necessary access for system processes to run OpenSSH correctly.

Step-by-Step Guide​

• Open Windows PowerShell as Administrator:
• Right-click on the Start button, then select "Windows Terminal (Admin)" or "PowerShell (Admin)".
• Backup Current Permissions (Optional but Recommended):
• It’s always a good idea to create a backup of existing ACL settings before making changes:
  

  powershell
  
       icacls "C:\ProgramData\ssh" /save ssh_permissions_backup.txt
  
       icacls "C:\ProgramData\ssh\logs" /save ssh_logs_permissions_backup.txt

• Update the Folder Permissions:
• Grant full control to the System folder and administrators, and ensure that authenticated users have at least read access. You can execute the following commands:
  

  powershell
  
       icacls "C:\ProgramData\ssh" /grant "Administrators:F" /grant "SYSTEM:F" /grant "Authenticated Users:R" /T
  
       icacls "C:\ProgramData\ssh\logs" /grant "Administrators:F" /grant "SYSTEM:F" /grant "Authenticated Users:R" /T

• The /T flag applies changes to all subfolders and files.
• Restart the SSH Service:
• After adjusting the permissions, restart the OpenSSH service to apply the changes:
  

  powershell
  
       Restart-Service sshd

• Test Your SSH Connection:
• Attempt to connect remotely to confirm that SSH is operating normally. If the connection works, the temporary fix is successful.

Note: If you encounter further issues or unexpected behavior, consider consulting official support channels or reverting the changes using your backups.

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Analysis and Broader Implications​

The Balancing Act of Security and Usability​

This incident underscores the delicate balancing act inherent in modern operating system updates. While security patches are essential to protect users, unexpected side effects like this can disrupt workflows, highlighting the challenges involved in large-scale software updates.

• User Vigilance: Always review update details, and if you rely heavily on specific services such as SSH, test updates in a controlled environment before widespread deployment.
• Backups and Rollbacks: Maintain consistent backups of system configurations and know how to revert settings if an update causes problems.
• Community Feedback: Open discussion forums and community feedback – as seen on WindowsForum.com – help disseminate temporary fixes and troubleshooting tips rapidly.

Remote Work and the Importance of SSH​

In the age of remote work, secure and stable remote connections are no longer a luxury but a necessity. Businesses and IT professionals depend on SSH for secure server management and remote troubleshooting. Interruptions in such essential services can impact:

• Network Security: Weakened remote management can leave systems exposed to additional risks.
• Operational Efficiency: Time spent troubleshooting these issues can delay critical updates and maintenance schedules.
• Overall Trust in Updates: Repeated issues may encourage users to delay or avoid applying future security patches, potentially increasing vulnerability to threats.

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Best Practices for Remote Administrators​

Given the issue and the temporary remedy discussed, consider these best practices to minimize downtime and safeguard your remote management setup:

• Stay Informed: Keep track of Microsoft's announcements and Windows 11 update logs. Subscribing to reputable tech news sources and community forums (like WindowsForum.com) can be invaluable.
• Regular Backups: Regularly back up your configuration files and system settings, especially before installing new updates.
• Test Environments: If possible, maintain a test lab environment to validate new updates. This helps in identifying issues like the SSH connection bug before they affect production systems.
• Document Workarounds: Share temporary fixes and workarounds within your IT community to help colleagues facing similar issues.
• Monitor Service Status: Use monitoring tools to keep an eye on vital services such as OpenSSH so that any disruption is flagged immediately.

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Conclusion​

While the Windows 11 SSH connection glitch represents a temporary setback, it also serves as a reminder of the complexities behind large-scale operating system updates. Microsoft’s swift action in addressing the issue and providing a temporary workaround illustrates its commitment to maintaining a secure and functional ecosystem for its users.
For now, those affected can follow the ACL adjustment instructions provided above to regain control of their remote connections. With a permanent patch expected in the coming weeks, remote administrators and everyday users alike can look forward to a more seamless experience with their Windows 11 systems.
Stay tuned to WindowsForum.com for further updates and detailed guides on dealing with Windows 11 updates, Microsoft security patches, and cybersecurity advisories. In the meantime, happy troubleshooting, and may your SSH connections remain strong and reliable!

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Remember: Keeping your system secure sometimes means dealing with unexpected issues—but with a little ingenuity and the right workaround, you can stay one step ahead of any disruption.

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Source: Ruetir https://www.ruetir.com/2025/02/22/windows-11-is-breaking-your-remote-connections-per-ssh-but-microsoft-already-works-on-the-solution/