Office 365 Outlook Desktop Application Search Not Working on macOS
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OUTLOOK
Close Outlook
SETTINGS
Add the profile folder, usually called "Main Profile" located inside the folder below to Spotlight Privacy
~/Library/Group Containers/UBF8T346G9.Office/Outlook/Outlook 15 Profiles/
Once the Profile Folder is Added, Remove the Profile Folder from Spotlight Privacy
*the idea behind adding the folder and then removing it is to force Spotlight to reindex the folder
COMMAND LINE
mdimport -L
OUTLOOK
Open Outlook and Search (The reindexing may take minutes to hours)