Thank you for the helpful comments, Victor.

> Have you tested the exact same credentials with an MUA such as
> Thunderbird, Outlook Express, Mail.app, ...

Yes, Outlook 2007 SMTP with identical settings and credentials.
I've included a screenshot of my exact settings, but they are
exactly what I described earlier.  I also used Wireshark to
verify that the same server:port 208.127.0.5:587 were the same
server Postfix is using.  http://cera.us/tmp/outlook_smtp.png

> Generally, you should have such relayhost names in [], both in main.cf
> and in the lookup key in smtp_sasl_password_maps.

Done.

>       chmod 0600 /etc/postfix/sasl/sasl_passwd*

Done.

There an invalid certificate mentioned in the postfix logs, but I
don't think this would affect anything with the authentication.

  Jul  4 12:54:34 psico postfix/smtp[31120]: certificate verification failed 
for smtpauth.exchangecarrier.net[208.127.0.5]:587: untrusted issuer 
/CN=owa1.exchangecarrier.net

I also tried [blindly] messing with different combinations of the
following options I read by other trouble-shooters on the net,
but none of them seemed to add anything new:
  smtp_sasl_security_options = noplaintext,noanonymous
  smtp_sasl_mechanism_filter = !gssapi, !external, static:all
  smtpd_sasl_authenticated_header = yes
  smtp_sasl_type=cyrus

> Either ch...@cera.us is not the right username, or the password
> in smtp_sasl_password_maps is not the right password or the
> server is not working.

I tried changing my password just in case, same problem.  The
username/password is still being printed correctly in the log
files (currently only numbers and letters), so I'm baffled.  I
also tried changing the password to something arbitrary, and the
error message is same "535 5.7.3 Authentication unsuccessful"

I would love to hear suggestions on what to try next.  I don't
know how to reverse-engineer the Outlook stream captured by
Wireshark, and possibly replay it with Postfix somehow.  It seems
there should be something simpler, so any additional pointers are
greatly appreciated. -Chris




* Victor Duchovni <victor.ducho...@morganstanley.com> [090704 20:05]:
> On Sat, Jul 04, 2009 at 02:29:51PM -0400, Chris Cera wrote:
> 
> > I'm having an issue relaying to DNAMail Exchange Server with
> > SASL.  I'm receiving the following error, despite being very
> > confident I have the correct credentials: 
> > 
> >   535 5.7.3 Authentication unsuccessful
> > 
> > smtp_sasl_password_maps = hash:/etc/postfix/sasl/sasl_passwd
> 
> Have you tested the exact same credentials with an MUA such as Thunderbird,
> Outlook Express, Mail.app, ...
> 
> If the server does not accept the credentials, your confidence is
> immaterial. Either ch...@cera.us is not the right username, or the
> password in smtp_sasl_password_maps is not the right password or
> the server is not working.
> 
> > Jul  4 12:54:35 psico postfix/smtp[31120]: > 
> > smtpauth.exchangecarrier.net[208.127.0.5]:587: AUTH NTLM 
> > TlRMTVNTUAABAAAABwIAAAAAAAAgAAAAAAAAACAAAAA=
> > Jul  4 12:54:35 psico postfix/smtp[31120]: < 
> > smtpauth.exchangecarrier.net[208.127.0.5]:587: 334 
> > TlRMTVNTUAACAAAACAAIADgAAAAFAoEChQG+04pLfAMAAAAAAAAAAKQApABAAAAABQLODgAAAA9NAEEASQBMAAIACABNAEEA
> > Jul  4 12:54:35 psico postfix/smtp[31120]: > 
> > smtpauth.exchangecarrier.net[208.127.0.5]:587: 
> > TlRMTVNTUAADAAAAAAAAAEAAAAAYABgAQAAAAAgACABYAAAAGgAaAGAAAAAAAAAAegAAAAAAAAB6AAAABQIAAIT+12cigyI2s9yxfVBRW+6DRa8UBCC6UE0AQQBJAEwAYwBoAHIAaQBzAEAAYwBlAHIAYQAuAHUAcwA=
> > Jul  4 12:54:40 psico postfix/smtp[31120]: < 
> > smtpauth.exchangecarrier.net[208.127.0.5]:587: 535 5.7.3 Authentication 
> > unsuccessful
> 
> The Challenge/response nature of NTLM makes it difficult to extract your
> password from the above, all one can say is that the server declined the
> handshake for ch...@cera.us, most likely because the username or password
> is not right, but perhaps something else is wrong. First test with Thunderbird
> or similar.
> 
> > relayhost = smtpauth.exchangecarrier.net:587
> 
> Generally, you should have such relayhost names in [], both in main.cf
> and in the lookup key in smtp_sasl_password_maps.
> 
>     main.cf:
>       relayhost = [smtpauth.exchangecarrier.net]:587
> 
>     sasl_password:
>       [smtpauth.exchangecarrier.net]:587      user:pass
> 
> > -rw-r--r-- 1 root root 51 2009-07-04 11:50 /etc/postfix/sasl/sasl_passwd
> > -rw-r--r-- 1 root root 12288 2009-07-04 14:09 
> > /etc/postfix/sasl/sasl_passwd.db
> 
> Should not be group or world readable:
>       
>       chmod 0600 /etc/postfix/sasl/sasl_passwd*
> 
> -- 
>       Viktor.
> 
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