Microsoft on-premises server product that runs Office Online.
Hi Joshua,
Thank you for sharing the additional details and the related thread.
Office 2016 connectivity to Microsoft 365 services has been unsupported since October 10, 2023, and Office 2016 reached end of support on October 14, 2025. Unsupported Office versions may experience compatibility, performance, or reliability issues over time and may become vulnerable to security threats because security updates are no longer available.
For further information: End of support resources for Office - Microsoft 365 Apps | Microsoft Learn
As these users receive a newly cloned VM whenever they sign in, I recommend that your IT team:
- Install all remaining available Windows 11 and Office 2016 updates in the VMware master image.
- Confirm that TLS 1.2 is enabled and that no proxy, firewall, web filtering, or SSL inspection service is interfering with Microsoft authentication endpoints.
- Test one affected account on a physical computer, persistent VM, or clean VM that does not use the current master image.
- Test the same account using Microsoft 365 Apps or another supported version of Office on a test VM.
If the same account signs in successfully with a supported Office version under the same network conditions, the practical resolution would be to upgrade the Office installation.
You may also refer to: Office versions and connectivity to Microsoft 365 services - Microsoft 365 Apps | Microsoft Learn
I hope this helps move the case forward. Should you have any further questions or need additional assistance, please feel free to share them in the comment below. I'm very happy to help.
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