For the record, I debugged the SMTP transaction today and solved it. It appears that Microsoft Outlook for Mac doesn't support the "plain" authentication method for outbound SMTP/SASL connections, even though it's fine for IMAP.
Changing the authentication mechanisms in /etc/dovecot/conf.d/10-auth.conf to
auth_mechanisms = plain login
fixed it.
On 2/13/18, 20:05, "Blind-sysadmins on behalf of Jason White via Blind-sysadmins" wrote:
This is mildly interesting: I have a Postfix server configured to offer SASL
on port 587. Dovecot is providing the SASL support. Microsoft Outlook 2016 for
Mac fails to send messages out via my server, reporting that it doesn't
support any of the available authentication methods. Meanwhile, Microsoft
Outlook for Windows can send messages via the server without any difficulties.
I've played with configuration settings, but with no luck. If I try to enable
logging on Outlook for Mac, various operations (including, crucially, creating
a new message) become unavailable, and it never seems to finish reading the
inbox. Without logging enabled, it's able to read IMAP folders fine.
This doesn't really matter - I have plenty of other ways of sending mail, even
when using the Mac, but if anyone here has clues about the mystery, I would be
interested.
It's worth noting that Outlook 2016 for Mac works reasonably well with
VoiceOver. Unfortunately, it doesn't implement equivalents to many of the
keyboard shortcuts (especially for commands in the ribbon) found in the
Windows version. Thus, for example, changing to a different folder is a slow
process - I haven't found a faster method than scrolling through the list with
cursor keys.
Nevertheless, someone at Microsoft has evidently been paying attention to its
accessibility, and that's a positive development.
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