Hi all hope well, wondering if someone would be so kind as to help.
So I have two computers, a desktop and a laptop. Both devices are logged into the same IMAP email account, (although the desktop has an additional number of accounts on it). the software is registered and logged into the same account also.
Initially in both cases here I will have the inbox selected of the same account.
The desktop is running MacOS Sequoia 15.7.1 with Microsoft Office H&B 2021, Version 16.102.3 (25110228). This is a recent install since late September so the drive has had maybe 5 weeks to complete indexing. The device and the software seem to run fine. Outlook is running in legacy mode.
The laptop is running MacOS Sequoia 15.7.1 with Microsoft Office H&B 2024, Version 16.102.3 (25110228). It has been installed for almost a year so way longer to complete any indexing.



I have re-indexed once on both machines after the office install to gee things up as I've found that Outlook search is always very flaky on a new install.

If I search for a single term in the 2021 version, the search is - and pretty much always has been very comprehensive).
As an example I search for the term, "Devenp" and I had 2133 results and these results were displayed regardless of date/mailbox/from or to.

I then altered the search slightly as follows, "to: Devenp" and I was presented with 231 results. I also of course had the option to further refine by using the advanced search facility.

Now on the 2024 version this is what happens;
When I search with the inbox selected I get 2 results. If I then select the sent box however and use exactly the same search term I get 16 results.

Anyway, back to the inbox for a moment. I change the search term to "to:devenp" and I get no results either whether inbox or sent box.

Devenp isn't at real word of course, it's part of somebody's name.
Any suggestions as to why this is so messed up would be much appreciated, this is the reason I'm still on 2021 on my main machine.

Do I understand correctly?

You have Legacy Outlook for Mac on your desktop and New Outlook for Mac on your laptop?

For the same Search on the same dataset, Legacy gives you lots of results but New only gives you a handful?

Hi there, thanks for picking this up.
You have absolutely got it correctly. I was going to paste screen shots but it's a PITA to have to do it from a URL as opposed to uploading it directly into this thread.
To add to that, the desktop has Office 2021 running in legacy mode and the laptop has Office 2024 where no legacy mode is available.

My first suggestion would be Mac In App Support
Contact support within Outlook for Mac - Microsoft Support

If they can't help, come back and we'll start digging around.

I'll give it a shot and update. Many thanks.