On Wed, Dec 11, 2013 at 06:17:08PM +1100, Mark Jamsek wrote:

> However, I cannot get SMTP authentication working, no matter what I
> try.

Still need those glasses...

> And, the glaringly obvious absence of SMTP auth mechanisms:
>
> 220 mail.bsdbox.co ESMTP Postfix
> ehlo bsdbox.co
> 250-mail.bsdbox.co
> 250-STARTTLS

Only when not using TLS.

> Just for good measure, here is maillog data immediately post
> receiving mail and replying:
> 
> Dec 11 07:11:31 mail postfix/smtp[65909]: connect to
> myune-edu-au.mail.eo.outlook.com[213.199.154.23]:25: Connection refused

This problem is a failure to *send* email out, that is already in
the queue.  Not failure to authenticate submission requests that
add mail to the queue.

> I've scrutinized and parsed my config files with all the relevant
> Postfix and Dovecot literature. I guess I am overlooking something
> blatantly obvious but I need a fresh set of eyes and some help. I've
> been at this all day and getting no where. Thanks, guys.

It helps if you actually look at your logs to see what they actually
say, rather than posting them without trying to read them.  You
can also look at your queue with "mailq", or "qshape" (available
with Postfix source).

You've got a firewall problem or similar, your network is blocking
connections to port 25 on that host.  I have no trouble connecting
to it:

    $ posttls-finger -o inet_protocols=ipv4 -Lsummary 
"[myune-edu-au.mail.eo.outlook.com]"
    posttls-finger: Connected to 
myune-edu-au.mail.eo.outlook.com[213.199.154.87]:25
    posttls-finger: < 220 DB3FFO11FD012.mail.protection.outlook.com Microsoft 
ESMTP MAIL Service ready at Wed, 11 Dec 2013 09:28:36 +0000
    posttls-finger: > EHLO amnesiac.example
    posttls-finger: < 250-DB3FFO11FD012.mail.protection.outlook.com Hello 
[192.0.2.1]
    posttls-finger: < 250-SIZE 157286400
    posttls-finger: < 250-PIPELINING
    posttls-finger: < 250-DSN
    posttls-finger: < 250-ENHANCEDSTATUSCODES
    posttls-finger: < 250-STARTTLS
    posttls-finger: < 250-AUTH
    posttls-finger: < 250-8BITMIME
    posttls-finger: < 250-BINARYMIME
    posttls-finger: < 250 CHUNKING
    posttls-finger: > STARTTLS
    posttls-finger: < 220 2.0.0 SMTP server ready
    posttls-finger: certificate verification failed for 
myune-edu-au.mail.eo.outlook.com[213.199.154.87]:25: untrusted issuer 
/C=IE/O=Baltimore/OU=CyberTrust/CN=Baltimore CyberTrust Root
    posttls-finger: Untrusted TLS connection established to 
myune-edu-au.mail.eo.outlook.com[213.199.154.87]:25: unknown with cipher 
AES128-SHA (128/128 bits)
    posttls-finger: > EHLO amnesiac.example
    posttls-finger: < 250-DB3FFO11FD012.mail.protection.outlook.com Hello 
[192.0.2.1]
    posttls-finger: < 250-SIZE 157286400
    posttls-finger: < 250-PIPELINING
    posttls-finger: < 250-DSN
    posttls-finger: < 250-ENHANCEDSTATUSCODES
    posttls-finger: < 250-AUTH LOGIN
    posttls-finger: < 250-8BITMIME
    posttls-finger: < 250-BINARYMIME
    posttls-finger: < 250 CHUNKING
    posttls-finger: > QUIT
    posttls-finger: < 221 2.0.0 Service closing transmission channel

-- 
        Viktor.

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