Hey BhamDesigner,
Clearing out caches and trying in safe mode were great steps! We recommend backing up your Mac, updating macOS, and the Outlook app to see if that helps to resolve this. Here are some guides to help with those steps, just in case:
- Use this resource for information on backing up your Mac: How to back up your Mac - Official Apple Support
- This will help with updating: Update macOS on Mac - Apple Support
- To update the Outlook app, if it was downloaded from the Mac App Store, this guide will help: Use the App Store to update apps on Mac - Apple Support
In addition to the above steps, this guide has more steps that can help with unexpected behavior when using an app: If an app freezes or quits unexpectedly on Mac - Apple Support
We also recommend reaching out to Microsoft Support to look into this with you too as they're the best resource for their software. Here's a link to their support, just in case: Microsoft Support
Thanks for using Apple Support Communities.
Take care!