On my Postfix server, when my co-workers VPN from their laptops from
home, they then send mail via Outlook and their ISP IP address. When
the message gets to it's recipient, it's marked ***SPAM*** by SA.
User's are complaining that email from internal users are being marked
as 'spam' and they don't know why. When I check the message source, I
can see that the user is connected to their personal ISP
(tampabay.res.rr.com in this case) to tunnel / VPN in and send mail
from their work account. My question is what can I fix to eliminate
this confusion for my co-workers w/o compromising actual spam to get
through? If this is good normal behavior from SA / Postfix, then I
will leave it alone based on your expect recommendations however if
you think I can tune Postfix / SA to handle mail better, I would
greatly appreciate any suggestions. I see below in the headers that
the message is being tagged as spam due to parameters that are typical
or big ISP's. The message source is below:

Return-Path: <el...@mydomain.tld>
X-Original-To: slacha...@mydomain.tld
Delivered-To: slacha...@mydomain.tld
Received: from localhost (localhost.localdomain [127.0.0.1])
                by mail.mydomain.tld (Postfix) with ESMTP id CD2D7778382;
                Mon, 12 Apr 2010 09:08:57 -0400 (EDT)
X-Virus-Scanned: amavisd-new at mydomain.tld
X-Spam-Flag: YES
X-Spam-Score: 5.266
X-Spam-Level: *****
X-Spam-Status: Yes, score=5.266 tagged_above=-999 required=5
                tests=[BAYES_00=-1.9, DOS_OUTLOOK_TO_MX=2.845,
                FSL_HELO_NON_FQDN_1=0.001, HELO_NO_DOMAIN=0.001,
RCVD_IN_PBL=3.335,
                RCVD_IN_SORBS_DUL=0.001, RDNS_DYNAMIC=0.982,
O_EQ_FM_DIRECT_MX=0.001]
                autolearn=no
Received: from mail.mydomain.tld ([127.0.0.1])
                by localhost (mydomain.tld [127.0.0.1]) (amavisd-new, port
10024)
                with LMTP id qDSvk1vgoHls; Mon, 12 Apr 2010 09:08:57 -0400
(EDT)
Received: from elugo2 (165-252.200-68.tampabay.res.rr.com [68.200.252.165])
                by mail.mydomain.tld (Postfix) with ESMTP id ABF3477838C;
                Mon, 12 Apr 2010 09:08:56 -0400 (EDT)
From: "Esteban Lugo" <el...@mydomain.tld>
To: "'Esteban Lugo'" <el...@mydomain.tld>,
                "'Richard'" <rich...@somedomain.tld>,
                "'Scott'" <s...@mydomain.tld>,
                "'David'" <d...@mydomain.tld>,
                "'Hassan'" <h...@mydomain.tld>,
                "'Travis'" <t...@mydomain.tld>
References: <000a01caa428$249ebb70$6ddc32...@org>
<75e1fe1c6e1c924a8f27e609cbe62c3d47e1394...@hvxmsp1.us.somedomain.tld>
In-Reply-To:
Subject: ***SPAM*** RE: WHL Request 4/12-4/16
Date: Mon, 12 Apr 2010 09:08:54 -0400
Message-ID: <000901cada41$4f7bc000$ee7340...@org>
MIME-Version: 1.0
Content-Type: multipart/mixed;
                boundary="----=_NextPart_000_000A_01CADA1F.C86A2000"
X-Mailer: Microsoft Office Outlook 12.0

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