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OS: 11.2.3

Outlook: v16.47

I have an Exchange account set up on Outlook that is showing inconsistent search results. When I search for from:Person1 the data comes back exactly as I would expect with messages sent to me by that person. Even messages from weeks ago. But when I try from:Person2 with more recent results I get no returns at all.

What's even weirder (IMO) is that when I search for just Person2 I do find the message I would expect to see, plus more as this doesn't have the from filter on it. But I don't get why this would come back with results and the from filter wouldn't. I can't identify a real pattern for when this happens outside of this seems to be happening for some senders and not others.

I googled around and tried repairing my search with these instructions and these instructions but neither has had any effect.

I have another Mac with the same account loaded on the same version of Outlook that shows the proper behavior. I also loaded this account onto the Mail app and it also is working as expected. So I'm pretty confident the issue is isolated to this Mac and this account but I can't find any resources for repair and I would think the index has had time to complete since the Mail app was able to start returning the search within a few minutes.

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