On 06/09/2018 12:58 PM, Mark Elkins via Exim-users wrote:
> Apple Maacbook running Microsoft Outlook can not connect to my exim
> based mail relay system using port 587, authentication and TLS.
>
[...]

> I cannot get this to work with my Macbook and MS
> Outlook as there is no setting for TLS encryption in MS Outlook for Mac.
> (believe you me, I have looked extensively).

https://support.office.com/en-us/article/IMAP-account-basic-settings-0A3F843D-D858-4527-BA0C-B57AEB83BF4E

mentions "Use SSL to connect" twice; once following "Incoming server"
and once following "Outgoing server".

It doesn't say whether it means STARTTLS or SSL-on-connect.  In case
it's the latter, port 465 is the usual place for that; keep STARTTLS
on 587.
-- 
Cheers,
  Jeremy

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