Windows Server 2016 has not been patched since September 2021

Question

Hello,

In our current setup, Windows Server 2016 has remained unpatched since September 2021. Despite attempts to install the February 2024 KB update, post-installation and reboot, the update gets reverted. Strikingly, even older updates such as those from November 2021 are experiencing the same issue, reverting upon installation and reboot.

How to fix and patch the server to the latest month ?

NOTE: The server is used in production environment.

Answer 1

Hi Aditya,

Certainly, I've encountered this issue with Windows Server 2016 updates reverting after installation at other client sites before. Based on those experiences, here's a step-by-step approach that has been effective in resolving such problems, especially in production environments:

Initial Checks and Preparations

Data Backup: First and foremost, ensure you have a complete backup of your server, including all critical data and the system state. This is crucial for recovery in case of unexpected issues.

Examine Update History: Look into the update history or the Event Viewer for specific error codes related to the update failures. These codes can be invaluable in diagnosing the problem.

Ensure Adequate Disk Space: Check that your system partition has sufficient space for the updates. Insufficient disk space is a common cause of update issues.

Run System File Checker: Open an elevated command prompt and execute sfc /scannow to scan for and repair any corrupted system files that might be hindering the update process.

Use DISM Tool: Another useful tool is DISM. Run DISM /Online /Cleanup-Image /RestoreHealth from an elevated command prompt to fix Windows corruption errors that could prevent updates from installing properly.

Troubleshooting and Fixing the Issue

Manual Update Installation: Sometimes, manually downloading and installing the update from the Microsoft Update Catalog can circumvent the issues seen with automatic updates.

Clean Boot for Update Installation: Initiating a clean boot reduces conflicts by using a minimal set of drivers and startup programs. This environment can often allow updates to install successfully.

Disable Conflicting Software: Interference from security software or other applications can block updates. Temporarily disabling such software (while understanding the security risks) might be necessary.

Run Windows Update Troubleshooter: This built-in tool can automatically find and fix problems with Windows Update, often resolving issues without further intervention.

Reset Windows Update Components: If problems persist, manually resetting the Windows Update components can help. This involves stopping the update service, clearing the cache, and restarting the service, effectively refreshing the update process.

Advanced Steps and Considerations

Log File Analysis: For deeper insight, examine the CBS.log and WindowsUpdate.log files. They can provide detailed error information that points to the root cause.

Minimize Production Impact: Any significant troubleshooting steps, especially those that might affect server availability, should be carefully planned to align with maintenance windows to minimize downtime.

Final Advice

Dealing with update issues in a production environment requires a careful and measured approach. Drawing from past experiences with similar problems, the steps outlined above have proven effective and I hope this helps on your side as well? If you have any further questions please let me know.