Operation timed out with smtp.gmail.com - please help

Anton Shterenlikht mexas at bristol.ac.uk
Fri Mar 29 18:33:05 UTC 2013


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 at bris.ac.uk>,
 ctladdr=<mexas at 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 at 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


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