After 3 days in, I came back to confirm search is still working on classic Outlook version 16.57 and Monterey 12.2.

The problem supposedly started after Monterey 12.1... Did you try to reindex the outlook mailbox ? It breaks from time to time : https://docs.microsoft.com/en-us/outlook/troubleshoot/outlook-for-mac/useful-tools

New outlook uses a different search engine, not based on spotlight, but it still does not support IMAP AFAIK, as well as on premises Exchange : https://support.microsoft.com/en-us/office/search-in-outlook-for-mac-returns-no-results-after-installing-macos-monterey-12-1-075c5f09-35db-4205-aba3-eea2f168c71b I am running Outlook preversion 16.57, and search works again and has been since friday. If it does not after updating Outlook, you might want to reindex the outlook part : https://docs.microsoft.com/en-us/outlook/troubleshoot/outlook-for-mac/useful-tools

Hi, thanks for pointing us to this Microsoft Article. At least it proves Microsoft recognized there is an issue here. Although I can technically switch to the new outlook, when I need to search an email, this is cumbersome, plus the new display makes me less efficient in this new outlook than the previous one. I tend to no see new emails in conversations for some reason. Also, the new Outlook does not work with automation yet and therefore cannot be used with Hook to create links to an email... Breaks my workflow...