Using older versions of Outlook for Mac in business environments
[Solved - at least temporarily till a fix is released]
I struggled with MS support for an hour and all I got was
- Reboot Outlook
- Reboot laptop
- Go back to Outlook 2011 because Outlook 365 has bugs (verbatim)
- It is a problem with Exchange server
Eventually, after playing around a bit, I realised that the problem goes away if logging is enabled in Outlook 365.
From the Ribbon, Goto Tools -> Sync Errors.
On the window that opens, click on the settings gear at the top right
Select "Turn on Logging for troubleshooting"
Click OK
Restart Outlook (you will see an annoying prompt each time you start Outlook, select to keep Logging On)
That's it, Outlook should stay synced now.