I recently migrated to a new MacBook Pro and discovered that searching in Outlook for Mac 2019 stopped working. I tried the various solutions people have suggested on the Internet, including creating a new Outlook profile and forcing Spotlight to reindex the message database, but they were ineffective.
What ended up working in my particular instance was to completely uninstall all traces of Office from my Mac per this Microsoft Support article, reboot, and then reinstall.
Please Note: This will clear all of your preferences and delete all of your Outlook data. If you are connected to a mail server (such as Gmail, Exchange or Office 365), you will be able to re-download your mail. Any local email/contacts/calendar events will be lost. This will also delete any customized Word templates.
From the Microsoft Support article:
Remove Office Applications
- Open Finder > Applications.
- Command+click to select all of the Office for Mac applications.
- Drag them to the Trash, or Ctrl+click an application you selected and click Move to Trash.
Remove files from your user Library folder
- In Finder, press Command+Shift+G.
- In the window that opens, enter ~/Library and then click Go.
- Open the Containers folder and Ctrl+click each of these folders and Move to Trash. Note that some of these folders may not be present.
- Click the back arrow to go back to the Library folder and open Group Containers. Ctrl+click each of these folders if present, and Move to Trash.
Finally, remove any Office applications from your Dock and restart your Mac.
Once your Mac has restarted, you'll be able to reinstall Office and your Outlook searching will (hopefully) work again.