Using New Outlook on Windows for personal email, calendar, and contact management
In new Outlook.
Navigate to Settings > General > Privacy and Data > Privacy Settings.
Enable Turn on experiences that analyze your content.
This fixed it for me. No idea how that setting got changed or if its new or something.
This worked for me. THANKS Pretty shameful this issue has not been addressed for a paid software and we have to run to forums to find a work around.