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

[Anton Shterenlikht]

	Date: Sat, 30 Mar 2013 07:49:19 -0400
	From: Jerry <jerry at seibercom.net>
	To: FreeBSD <freebsd-questions at freebsd.org>
	Subject: Re: Operation timed out with smtp.gmail.com - please help

	On Sat, 30 Mar 2013 10:49:45 +0000
	Matthew Seaman articulated:

	> Given you're seeing that CONNECTED message there, it certainly does.
	> The problem with that openssl command seems to be the 'unable to get
	> local issuer certificate' part.  That's possibly openssl being pickier
	> about verifying certs than sendmail would be, but that certificate
	> verification step is probably where you're coming adrift.  You need to
	> have the intermediate certs used by Google in your cacert.pem file, so
	> sendmail will trust the smtp.gmail.com cert.  Check the 'confCACERT'
	> setting in your sendmail.mc.  I have a block of code like this:
	>=20
	> define(`CERT_DIR', `MAIL_SETTINGS_DIR`'certs')dnl
	> define(`confCACERT_PATH', `CERT_DIR')dnl
	> define(`confCACERT', `CERT_DIR/cacert.pem')dnl
	> define(`confSERVER_CERT', `CERT_DIR/cert.pem')dnl
	> define(`confSERVER_KEY', `CERT_DIR/key.pem')dnl
	> define(`confCLIENT_CERT', `CERT_DIR/cert.pem')dnl
	> define(`confCLIENT_KEY', `CERT_DIR/key.pem')dnl
	>=20
	> which allows me to put all the keys and certs in /etc/mail/certs/

	If you really need the Gmail certs, you can use this to get them:

	openssl s_client -connect smtp.gmail.com:587 -starttls smtp -showcerts

	If you feel you really need the "Equifax Secure Certificate Authority"
	pem, go here <http://www.geotrust.com/resources/root-certificates/> and
	download it.

	Again, how to set up Sendmail is a task I leave for the student.

Jerry, Matthew, thank you

I think I got it working.
In addition to your advice, this guide was very helpful:

http://www.phinesolutions.com/sendmail-gmail-smtp-relay-howto.html

It seems these two options were required:

define(`RELAY_MAILER_ARGS', `TCP $h 587')
define(`ESMTP_MAILER_ARGS', `TCP $h 587')

Thanks again

Anton