I've checked Microsoft's Support Tools, but none of them seem to be relevant. I'm wondering if the Mac version, Outlook for Mac (2016), has any sort of feature parity for the "Connection Status" window. However, if the mail client is functioning properly, I can see a "BEARER" displayed in the "Authn" column. If the authentication is broken, I can tell it's getting stuck negotiating the connection, because it displays a "NEGO" status in the "Authn" column. In Windows Outlook, I've been able to check if a client is properly authenticated by checking the "Authn" authentication column in Outlook's "Connection Status" window (See Microsoft's documentation here). This has caused a lot of issues for users, with previously configured mail clients not properly negotiating connections with the mail servers.
At the University where I work, we've recently made the switch to Modern Authentication.
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