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Date:      Sat, 30 Mar 2013 07:49:19 -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:  <20130330074919.7902b8c2@scorpio>
In-Reply-To: <5156C349.9010004@FreeBSD.org>
References:  <201303301014.r2UAEi1W081669@zzz.men.bris.ac.uk> <5156C349.9010004@FreeBSD.org>

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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.

--=20
Jerry =E2=99=94

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