Windows Server Essentials Dashboard integration with Office 365 stops working after 24 hours in Windows Server 2012 R2 Essentials

Question

A recent problem we are having is that after 24 hours, the Office 365 integration feature of the Windows Server Essentials Dashboard stops working in Windows Server 2012 R2 Essentials.

On the Users tab of the Windows Server Essentials Dashboard, the Microsoft Online Account column for all users will change to "unknown", instead of displaying the email address of the linked online account.

Restarting the system, re-entering the Office 365 admin account credentials in the Dashboard, or just restarting the "Windows Server Essentials Email Service" allows the integration to work again for a while, but after 24 hours it stops working once again.

This issue started happening in February 2022 (perhaps after the February Windows Updates we installed--not sure). Office 365 support suggested trying Microsoft Q&A or paid support since this seemed to be an onsite server problem. We don't yet use MFA or modern authentication in Office 365 (tenant was created around 2012).

Has anyone else had recent issues with the Office 365 integration of Windows Server 2012 R2 Essentials? We've seen mention of a similar "24 hour" kind of problem with Windows Server 2016 Essentials, but not with Windows Server 2012 R2 Essentials.

Answer 1

Hi there,

This is a known issue and there are several users who have faced a similar issue. Below is some workaround that has helped them.

Check below registry key and make sure that the key “Value date” is Windows Server 2016 Essentials’ FQDN (system – full computer name):

HKEY_LOCAL_MACHINE\SOFTWARE\Microsoft\Windows Server\ADContext

Below threads discusses the same issue and you can try out some troubleshooting steps from this and see if that helps you to sort the Issue.

Windows Server 2016 Essentials Dashboard can't integrate with Office 365 https://learn.microsoft.com/en-us/answers/questions/342869/windows-server-2016-essentials-dasboard-can39t-int.html

Office 365 Integration fails with "Cannot connect to Microsoft online services" in Windows Server 2012 R2 Essentials https://learn.microsoft.com/en-us/archive/blogs/sbs/office-365-integration-fails-with-cannot-connect-to-microsoft-online-services-in-windows-server-2012-r2-essentials

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Answer 2

Some ideas here.
https://social.technet.microsoft.com/Forums/en-US/84dac8f4-fc03-4946-b21e-51c5399fba64/windows-server-essentials-dashboard-stopped-syncing-office-365-accounts?forum=winserveressentials

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