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Date:      Sat, 13 Jul 2002 16:42:11 -0700
From:      Gregory Neil Shapiro <gshapiro@FreeBSD.ORG>
To:        Terry Lambert <tlambert2@mindspring.com>
Cc:        freebsd-arch@FreeBSD.ORG
Subject:   Re: Mail subsystem defaults, adding authentication.
Message-ID:  <15664.47827.844708.151118@monkeyboy.gshapiro.net>
In-Reply-To: <3D300FD4.7479A8E5@mindspring.com>
References:  <20020713034725.GB47677@ussenterprise.ufp.org> <3D2FAFB2.E2E9CF36@mindspring.com> <20020713045704.GA49379@ussenterprise.ufp.org> <3D300FD4.7479A8E5@mindspring.com>

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tlambert2> You need to submit your patches for this to the sendmail people.
tlambert2> Without modification, sendmail does not enforce use of SSL for
tlambert2> permitting advertisement of SMTP AUTH, and therefore addition of
tlambert2> a pseudo-RFC-2595 "PLAIN" or "EXTERNAL X-UNIX" mechansim can not
tlambert2> reasonably be added to FreeBSD so that it's operational by default.

tlambert2> The STARTTLS SMTP command doesn't work, because it is issued
tlambert2> after the EHLO, which solicits the capabilities list that exposes
tlambert2> the SMTP AUTH.  The only method that works, therefore, is to use
tlambert2> an SSL connection -- SMTPS... port 465, instead of port 25).  You
tlambert2> can see the order of operation problem, I hope?

You need to go back and read the RFC's/documentation.

First, you can limit the AUTH mechanisms offered based on whether STARTTLS
was used or not.  Second, after a successful STARTTLS negotiation, a new
EHLO is done and a new set of AUTH mechanisms is given.

You can (and should) use STARTTLS with SMTP AUTH PLAIN/LOGIN and do not
(and should not) use SMTP over SSL as it is non-standard.

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