Microsoft recently reported that search in ‘old’ versions of Outlook for Mac returned no results after installing the macOS Monterey 12.1 update. This is said to have been fixed by installing the latest Office for Mac updates:
This exact thing has happened to me a few times with Outlook lately and I’ve failed to troubleshoot it. It seems to be somehow related to Spotlight indexing so a solution is to have it reindex and, after a while, it seems to work again. I do agree its incredibly frustrating.
I’m not sure recent updates have addressed this adequately but hopefully it will go away at some point.
I’ve had this using Outlook as well where it just wasn’t returning emails that I knew I’d been sent - compounded by the fact that the University has now added (staff) to the end of everyone’s name, so that we know we’re emailing a staff member - so now accepting the default name when you start your search returns no results, as the previous emails were just sent with the persons name and didn’t include the (staff) in the name!
I’ve resorted to undertaking in depth searches using Postbox - I would use that completely, but calendar invites are a bit funky in that and wants me to go to outlook on the web to accept. I tried Mailmate, and it seems to work with the 2FA that the University has in place, but saves two copies of an email on the server, so it’s a bit of a pain to use.
Unfortunately I don’t use Mail. I was never able to successfully able to setup my required HTML signature with it, so had to pass. Mind, I should have added “sent from my iPad” and no one would have noticed!