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Date: Sat, 21 Nov 2009 13:23:58 -0500
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From: Michael Proto <mike@jellydonut.org>
To: Victor Lyapunov <fullblaststorm@gmail.com>
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Cc: freebsd-pf@freebsd.org
Subject: Re: sending mail with attachments always fails (FreeBSD/pf)
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On Sat, Nov 21, 2009 at 1:07 PM, Victor Lyapunov
<fullblaststorm@gmail.com> wrote:

> rule 4/0(match): pass out on em0: (tos 0x0, ttl 127, id 19860, offset
> 0, flags [DF], proto TCP (6), length 48) 192.168.0.5.1822 >
> 209.85.129.111.465: =A0tcp 28 [bad hdr length 0 - too short, < 20]

This looks to be your problem-- bad hdr length 0. I don't know enough
of what mailer(s) you're using to relay this message outbound, but
since port 465 is smtp over TLS/SSL are you sure your smtp encryption
is working correctly? I often see these types of errors with other
TLS/SSL apps when one side is expecting an encrypted connection and
the other is not (correctly) providing it.

Have you tried using unencrypted smtp on port 25? Does that work?


-Proto