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Date:      Fri, 29 Mar 2013 15:36:19 -0400
From:      Jerry <jerry@seibercom.net>
To:        FreeBSD <freebsd-questions@freebsd.org>
Subject:   Re: Operation timed out with smtp.gmail.com - please help
Message-ID:  <20130329153619.69c5b4dd@scorpio>
In-Reply-To: <201303291832.r2TIWYPW035723@zzz.men.bris.ac.uk>
References:  <201303291832.r2TIWYPW035723@zzz.men.bris.ac.uk>

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On Fri, 29 Mar 2013 18:32:34 GMT
Anton Shterenlikht articulated:

> Please help debug sendmail / smtp.gmail config.
> 
> My University just switched to gmail (dickheads)
> and I'm trying to figure out how to set it up.
> 
> It used to work ok with the University smtp auth
> server. Now I get in /var/log/maillog:
> 
>  sm-mta[72300]: r2TI0vQc072134: to=<mexas@bris.ac.uk>,
>  ctladdr=<mexas@xxxx.men.bris.ac.uk> (1001/1001),
>  delay=00:20:01, xdelay=00:00:00, mailer=relay, pri=210424,
>  relay=smtp.gmail.com, dsn=4.0.0,
>  stat=Deferred: Operation timed out with smtp.gmail.com
> 
> I switched the firewall off completely.
> 
> I have:
> 
> # cat /etc/mail/auth/client-info
> AuthInfo:smtp.gmail.com "U:root" "I:mexas@bristol.ac.uk" "P:xxxxx"
> # 
> 
> and this in /etc/mail/freebsd.mc:
> 
> define(`confAUTH_MECHANISMS', `GSSAPI DIGEST-MD5 CRAM-MD5 LOGIN')dnl
> define(`SMART_HOST', `smtp.gmail.com')dnl
> 
> I rebuilt (run make under /etc/mail. This just
> renames freebsd.mc to <hostname>.mc, and freebsd.submit.mc
> to <hostname>.submit.mc) and restarted sendmail.
> 
> I also use:
> 
> MASQUERADE_AS(`bristol.ac.uk')
> MASQUERADE_DOMAIN(`bristol.ac.uk')
> 
> to use the university domain instead of
> may xxxx.men.bris.ac.uk, which is not
> acceptable.

Try this at the command line:

openssl s_client -connect smtp.gmail.com:25 -starttls smtp

If it times out, change the port number to 587 and try it again. If you
cannot make a connect using either port number then you have a firewall
problem.

-- 
Jerry ♔

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