For that, first you need to close the Outlook 2019 application, which is working on Mac OS and run Outlook Search Repair Troubleshooter. If the above workarounds did not help you to fix Outlook 2019 Mac search not working issue, then try to run Microsoft Outlook Search Troubleshooter. Approach #4: Execute Outlook 2019 Mac Search Troubleshooter. Top Hits is listed first in the results, and reflects messages you’ve read and replied to recently, your VIP senders and contacts, and other factors. You can search for email messages in any or all mailboxes by using your own words-such as “emails from John sent yesterday”-or by using Mail suggestions and search filters.