Using Classic Outlook on Windows for personal email, calendar, and contact management
I use office 365 ProPlus and had the same issue.
I found a solution that worked for me: disabling all add-ins in Outlook and then enabling them back.
- In Outlook, go to File->Options->Add-ins
- Click on Go (right to "COM Add-ins") and un-check all add-ins that are checked in the list.
- Click OK and exit from Outlook (File->Exit)
- Run outlook and verify that the problem is solved.
- I repeated stage 2 to 4 but this time checked all add-ins back and the problem seems to be solved.
Hope it will work for you too.