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Date: Fri, 29 Mar 2013 18:32:34 GMT
From: Anton Shterenlikht <mexas@bristol.ac.uk>
Message-Id: <201303291832.r2TIWYPW035723@zzz.men.bris.ac.uk>
To: freebsd-questions@freebsd.org
Subject: Operation timed out with smtp.gmail.com - please help
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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.

What else am I missing?

Thanks

Anton