Hi @Gerald Alena
Thank you for posting your question in the Microsoft Q&A forum.
To help narrow down the issue, could you please confirm whether you're using an Exchange or IMAP account? IMAP search functionality might be broken and not work as expected.
If you're not using IMAP, here are a few troubleshooting steps you can try:
When Outlook cannot search email addresses, autocomplete queries, or locate calendar events, it often signals a common issue related to search indexing or profile data, as AnjolaOluwa mentioned earlier.
-First, try restarting your Outlook and Windows system to see if that resolves the issue.
Go to Start > Settings > Troubleshoot > Other troubleshooters > Search and Indexing > Run to let Windows detect and repair common search issues.
-Verify indexing status:
Open Outlook > Search box > Search Tools > Indexing Status.

You should see the number of items remaining to be indexed:

If Outlook has not finished indexing, note the number of items remaining, wait 5 minutes, and check again. If the number of items has not decreased, proceed to the next step.
-If indexing does not progress, rebuild the Outlook Search Index by following this article: Fix search issues by rebuilding your Instant Search catalog - Microsoft Support.
-If these steps don't resolve the issue, consider creating a new Outlook profile. Sometimes, a corrupted profile can cause search problems.
-Additionally, you may try open Outlook in safe mode to check if one of your add-ins might be interfering.
For more information, you may take this article as a reference Troubleshooting Outlook search issues - Microsoft Support.
I hope this helps! If you have any other questions, feel free to ask.
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