Dear @Dale Jalovec,
Welcome to Microsoft Q&A Forum!
Thank you for sharing the details of your search issue. Therefore, I have several suggestions that you can try to see if they can help:
1.Try Outlook Web App (OWA): please log in to your mailbox via [Outlook on the Web] and perform the same search.
- If the search works in OWA, this confirms the issue is with the Outlook desktop app.
- You can use OWA as a temporary workaround while we fix the desktop client.
2.Then you try troubleshooting Outlook Desktop Search:
Please follow the steps in this official Microsoft guide: Troubleshooting Outlook search issues – Microsoft Support
This includes:
- Checking indexing status
- Rebuilding the search catalog
- Repairing Outlook installation if needed
Besides that, I find an article related to verify and rebuild the search index on the server side in Exchange Online: Rebuild search index of a mailbox in Exchange Online | Microsoft Community Hub
Additionally, there is an idea to fix search issues by rebuilding your Instant Search catalog, see more details in here: Fix search issues by rebuilding your Instant Search catalog - Microsoft Support
I hope this information can help you to solve it. Please feel free to update to me in the comment section. Wish you a nice day!
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