On Sun, Jul 24, 2016 at 01:59:25PM -0500, techlist06 wrote:

> But if I try to send from Outlook to port 587, the connection fails.

Many versions of Outlook don't support port 587 STARTTLS submission,
they only support wrappner mode on port 465.

> Outlook's "Test account settings" reports: "Send test e-mail message: None
> of the authentication methods supported by this client are supported by your
> server."

The server did not offer SASL "AUTH" in its EHLO reply.  Perhaps
Outlook does not support delayed "AUTH" advertisement after STARTTLS,
however see below.

> Jul 24 13:35:11 tn2 postfix/smtpd[9553]: > 220 tn2.myserver.com ESMTP Postfix
> Jul 24 13:35:11 tn2 postfix/smtpd[9553]: < EHLO HDPLEX2
> Jul 24 13:35:11 tn2 postfix/smtpd[9553]: > 250-tn2.myserver.com
> Jul 24 13:35:11 tn2 postfix/smtpd[9553]: > 250-PIPELINING
> Jul 24 13:35:11 tn2 postfix/smtpd[9553]: > 250-SIZE 10240000
> Jul 24 13:35:11 tn2 postfix/smtpd[9553]: > 250-ETRN
> Jul 24 13:35:11 tn2 postfix/smtpd[9553]: > 250-STARTTLS
> Jul 24 13:35:11 tn2 postfix/smtpd[9553]: > 250-ENHANCEDSTATUSCODES
> Jul 24 13:35:11 tn2 postfix/smtpd[9553]: > 250-8BITMIME
> Jul 24 13:35:11 tn2 postfix/smtpd[9553]: > 250 DSN
> Jul 24 13:35:11 tn2 postfix/smtpd[9553]: smtp_get: EOF

Client gives up after EHLO and before STARTTLS, perhaps because
"AUTH" is missing, however you don't have "smtpd_tls_auth_only =
yes", in your reported configuration, so if SASL is enabled at
compile-time, perhaps your dovecot auth socket is not configured
in the correct location or has the wrong permissions.  There
would then be warnings in the logs related to that problem.

Otherwise, the absense of "AUTH" in the EHLO reply might be
a configuration issue with dovecot, or is rather mysterious.

Perhaps you're reporting something other than the configuration
that Outlook is talking to.

-- 
        Viktor.

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