I just found this issue when I were supporting one of my client.
I recommended you that you should not use the legacy version of the outlook app if you are using Mac OS.
If you select file label and send the mail in the legacy outlook, the mail can't be delivered or the recipient can't check your message.
See below.
https://learn.microsoft.com/en-us/officeupdates/release-notes-office-for-mac#march-14-2023
Well it says it has been updated. But it dosen't mean the legacy version.
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