Hi @Michael Jansen
Thank you for posting your question in the Microsoft Q&A forum.
Based on your description, this looks like you've encountered an issue that Outlook search stops functioning properly after certain macOS updates.
Legacy Outlook for Mac relies entirely on macOS Spotlight for indexing and search. When Spotlight indexing is incomplete, restricted by privacy controls, or affected by changes introduced in a new macOS release, Outlook search can return no results, even though mail data is present and the Outlook database is healthy.
Since you’ve already rebuilt both the Spotlight index and the Outlook database using the steps in Troubleshoot search issues in Outlook for Mac - Microsoft Support, there are no additional troubleshooting options available for Legacy Outlook in this scenario.
If the issue persists, a workaround is to use Outlook on the web (OWA) to search and access mailbox content at https://outlook.office.com. OWA uses Microsoft’s server-side search, so it is not affected by macOS Spotlight indexing issues.
For a long‑term fix, the recommended approach is to switch to the New Outlook for Mac, which uses Microsoft’s own search service rather than Spotlight and is fully supported on newer macOS versions.
Hope this helps clarify the situation and gives you a path forward.
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