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If search problem persists, it is recommended to completely reset and rebuild the index of Windows Search service.
How to Rebuild/Reset Outlook Search Index? Check Outlook index status as shown above and try to search something.
Give Outlook some time to complete the full indexing (it depends on the number and size of mailboxes and connected PST files). Check Microsoft Outlook in the indexing options and save the changes. Now you need to enable Outlook Indexing in Search Settings, which was previously disabled. Open an elevated PowerShell console and restart the WSearch service: