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Date:      Sat, 30 Mar 2013 10:17:55 -0700 (PDT)
From:      Anton Shterenlikht <>
Subject:   Re: Operation timed out with - please help
Message-ID:  <>
In-Reply-To: <20130330074919.7902b8c2@scorpio>

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	Date: Sat, 30 Mar 2013 07:49:19 -0400
	From: Jerry <>
	To: FreeBSD <>
	Subject: Re: Operation timed out with - 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 cert.  Check the 'confCACERT'
	> setting in your  I have a block of code like this:
	> 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
	> 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 -starttls smtp -showcerts

	If you feel you really need the "Equifax Secure Certificate Authority"
	pem, go here <>; 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:

It seems these two options were required:

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

Thanks again


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