Sorry for the delay, I didn't see notice of your response.
Outlook is 16.0.5110.1001. When you say updated to the latest version of the desktop client, are you referring to the latest patches?
Nothing has been changed in the environment or on the client, except of disabling some unneeded add-ins but this was done in effort to troubleshoot the existing issue. One of which is an anti-virus client in. The add-ins currently running are the bare minimum needed.
It may be difficult to have the user use their Outlook in safe/mode throughout the course of the day, because the issue is intermittent we don't know exactly what triggers the issue. And not having the add-ins would affect their workflow.
The Outlook repair is a good approach. I will try that next.
Just to note I have also tried creating new Outlook profile and resetting the views with no success.
I will try to get that done today and report back tomorrow.