Re: Authentication unsuccessful relaying from Postfix to Microsoft ESMTP MAIL Service



On Sun, 09 May 2010 17:06:52 +0100, Clive Standbridge wrote:

I'm trying in vain to relay external mail from postfix on a Debian lenny
machine to a Microsoft SMTP server on the Internet. I've been reading
and searching for days. I've tried numerous combinations of settings
although I'm note certain what they all do and am experiencing
information overload.

O.k. Then you need to setup Postfix SSL/TLS acting as client, not server.

(...)

When I change relayhost to NEWSERVER:587, the mail gets stuck in
postfix. In /var/log/mail.log I see "Authentication unsuccessful".

(...)

So my questions are:
* How can I fix this in Postfix?

Let's see the logs...

* Can Postfix do this? Or do I need to change to something else e.g.
Exim?

Yes, you can setup Postfix for this.

* What does IceDove do that Postfix doesn't?

Logs will tell.

The rest of this mail contains more detail.

I've tried with:
* smtp_sasl_security_options set to noanonymous and empty *
smtp_tls_security_level set to "may", "none", "encrypt" and not set. *
relayhost set to NEWSERVER:587 and [NEWSERVER]:587 in main.cf and
sasl_passwd (kept them in step and updated sasl_passwd.db each time)

The doc you have to follow stands here:

http://www.postfix.org/SASL_README.html#client_sasl

/var/log/mail.log:

(...)

May 9 16:30:01 rimmer postfix/smtp[10643]: certificate verification failed for NEWSERVER[NEWSERVER-IPADDR]:587: untrusted issuer /L=ValiCert Validation Network/O=ValiCert, Inc./OU=ValiCert Class 2 Policy Validation Authority/CN=http://www.valicert.com//emailAddress=info@xxxxxxxxxxxx

Server replies that does not trust the issuer of that CA.

(...)

May 9 16:30:01 rimmer postfix/smtp[10643]: Untrusted TLS connection established to NEWSERVER[NEWSERVER-IPADDR]:587: TLSv1 with cipher RC4-MD5 (128/128 bits)

I guess your are having problems with the certificate itself. It cannot
be verified by the remote server.

Note: I think Thunderbird uses its own SSL CA root certificates database...

Greetings,

--
Camaleón


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