Hi everyone,
I've been experiencing search issues with Outlook Version 16.85.2 (Legacy, as the new Outlook has font issues) on macOS Sonoma. I was able to fully resolve these problems by contacting Microsoft and using the following commands in the terminal:
sudo mdutil -a -i off
sudo launchctl unload -w /System/Library/LaunchDaemons/com.apple.metadata.mds.plist
sudo launchctl load -w /System/Library/LaunchDaemons/com.apple.metadata.mds.plist
sudo mdutil -a -i on
These commands will reindex your entire Mac, which may take a few minutes to a few hours depending on your files and system specifications.
I hope this helps anyone facing similar issues with Outlook search.
Thanks