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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