Sendmail and "Proper Authentication"

[Chuck Swiger]

On Aug 23, 2006, at 8:50 PM, Nicholas Ink wrote:
> The first problem I experienced was that there a host name lookup
> failure for "gmail.com," which I have subsequently corrected by adding
> the line:
>
> gmail.com       smtp:[smtp.gmail.com]
>
> to /etc/mail/mailertable.

This is wrong; you should be using an IP address inside the domain- 
literal form (square brackets).

You should try to fix whatever the problem with your DNS is, instead.
"dig -t mx gmail.com" should return valid results....

> However, there is still a problem, when I
> try to send an e-mail, /var/log/maillog says:
>
> Aug 23 23:18:08 arches sm-mta[1049]: k7O3I7K2001049:
> from=<nink at XXXXXXXX.xxx>, size=397, class=0, nrcpts=1,
> msgid=<44ED1A6F.1090009 at XXXXXXXX.xxx>, proto=ESMTP, daemon=IPv6,
> relay=localhost [IPv6:::1]
>
> Aug 23 23:18:16 arches sm-mta[1051]: STARTTLS=client,
> relay=gmail-smtp.l.google.com., version=TLSv1/SSLv3, verify=FAIL,
> cipher=DES-CBC3-SHA, bits=168/168
>
> Aug 23 23:18:16 arches sm-mta[1051]: k7O3I7K2001049:
> to=<nicholasink at gmail.com>, ctladdr=<nink at XXXXXXXX.xxx> (1007/0),
> delay=00:00:08, xdelay=00:00:08, mailer=smtp, pri=30397,
> relay=gmail-smtp.l.google.com. [66.249.83.111], dsn=5.0.0,
> stat=Service unavailable
>
> Aug 23 23:18:16 arches sm-mta[1051]: k7O3I7K2001049: k7O3IGK2001051:
> DSN: Service unavailable
>
> where arches is my host name.  I can't understand why it continues to
> say "Service unavailable" when I know Gmail is not experiencing any
> downtime or anything else.  Is this some sort of spam filter?

Yes, on their side.  gmail.com isn't going to relay random email  
without you authenticating first, probably; look into configuring  
SMTP AUTH on your side, or talk with <postmaster at gmail.com> about  
what their requirements are to permit you to relay via their mail  
servers.

However, normally people configure their machines to relay email via  
the SMTP server(s) which your ISP provides, as they are generally  
configured to trust their client networks without requiring SMTP AUTH  
and thus are easier to use...

-- 
-Chuck