FIX: Microsoft 365 and Outlook Applications Crashing on Windows Server 2016

Recently, many organizations running Microsoft 365 applications on Windows Server 2016 experienced an unexpected and frustrating global issue: applications like Outlook began crashing unexpectedly.

While Microsoft has since issued official fixes, administrators needed an immediate workaround to restore user productivity. This guide details the essential troubleshooting steps and the command-line fix provided by Microsoft for this specific M365 application stability problem.

The Primary Solution: Updating Microsoft 365 via Command Line

The most effective and immediate workaround provided by Microsoft involves running a specific command to force the Office application to update to a stable version.

This method bypasses automatic updates and targets the specific components causing the instability.

Step-by-Step Fix:

Open Command Prompt: Open the Command Prompt as an Administrator on the affected Windows Server 2016 device.
Execute the Update Command: Copy and paste the following command into the Command Prompt and press Enter. This command instructs the Office Deployment Tool to update the application installation:Bash"C:\Program Files\Common Files\Microsoft Shared\ClickToRun\OfficeC2RClient.exe" /update user updatetoversion=16.0.18227.20105 Note: The version number (e.g., 16.0.18227.20105) is the target stable version that resolves the crashing issue [01:05].
Restart the System: After the command finishes executing and updating the Office application, restart the Windows Server 2016 device [01:20].

Once the system is back up, your Microsoft 365 applications should launch and function without the previous crashing issues.

Verifying the Issue Status

For ongoing updates and to verify the status of any global service issue, administrators should always check the Microsoft 365 Admin Center.

Log in to admin.microsoft.com.
Navigate to Service Health.
Look for messages related to M365 applications and Windows Server 2016. Microsoft posts official updates, workarounds, and final resolution confirmation here [01:45].

Alternative Troubleshooting (The Last Resort)

If the command-line update fails to resolve the crashing issue, the problem might stem from a deeper corruption in the Office installation.

The final troubleshooting step is a complete reinstallation:

Perform a complete uninstallation of the Microsoft Office application suite.
Reinstall the application suite from your Microsoft 365 portal.

While time-consuming, a clean reinstallation often resolves complex stability issues that patches or updates cannot fix [02:11].