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I have the same problem as yourself. My work email will not work in Outlook 2016 (15.14.2). In the accounts list it has yellow bullet status. In addition....I can send email through the account but not receive anything....of course it does not create the IMAP folder structure plus it clearly says at the status bar at the bottom...'not connected to <mail server of my work email>'

The funny part is that both Yahoo and Gmail work perfectly well on IMAP in my Outlook 2016.

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Talking moose,

.....thats the typical support questions you ask back....'Did you turn the power on to the computer...etc?'. I am sure you can do better

If you use the same incoming and outgoing server settings as in iPhone why would it still not work? As for me I have NO firewalls blocking anything and to make matters more confusing I tried using Apple's own Mail on the same laptop and works like a charm.

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My general guess is that it probably has to do with the client certificate management software of MS Outlook 2016 playing some form of game. If the certificate is wrong/not accepted by Outlook (regardless what you as an administrator click/allow/trust, etc) it will NOT connect.

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I think this can only be solved by the rookies who implemented the Outlook software and clearly didn't test it through thoroughly.