Received your e-mail and responding with a copy of the message header.
Header of message which I received from you clearly shows that TLS 1.2 was used to send message:
Return-Path: <REDACTED@digitaliway.com>
Received: from mail.digitaliway.net (mail.digitaliway.net [208.75.248.202]) by securemail.chicagonettech.com with SMTP
(version=TLS\Tls12 <=== SmarterMail shows that TLS 1.2 was used for transaction
cipher=Aes256 bits=256);
Wed, 2 Sep 2015 06:56:01 -0500
DomainKey-Signature: a=rsa-sha1; c=simple; q=dns;
d=digitaliway.com; s=digitaliway;
h=received:from:to:subject:date:message-id:mime-version
:content-type:x-mailer:thread-index:content-language
:x-messagesniffer-identifier:x-gbudb-analysis
:x-messagesniffer-scan-result:x-messagesniffer-rules
:x-declude-sender:x-declude-spoolname:x-declude-refid
:x-declude-note:x-declude-scan:x-declude-tests:x-country-chain
:x-declude-code:x-helo:x-identity;
b=RxXBMCJDVpJ8pIurW+fbBWh1Anyzz5WB1vcSwVTYkA7X62x5xI8NUgr+MKF4w53jV
/ijtDlyHIcDXl/cqQGEZh7hsqFDVBDe/85eb997u1PXSEai0CoK7RGaIVxraI9h
DKIM-Signature: v=1; a=rsa-sha256; c=relaxed/relaxed;
d=digitaliway.com; s=digitaliway;
h=x-identity:x-helo:x-declude-code:x-country-chain:x-declude-tests
:x-declude-scan:x-declude-note:x-declude-refid
:x-declude-spoolname:x-declude-sender:x-messagesniffer-rules
:x-messagesniffer-scan-result:x-gbudb-analysis
:x-messagesniffer-identifier:content-language:thread-index
:x-mailer:content-type:mime-version:message-id:date:subject:to
:from;
bh=ElgnKLjTgOTyifodwMRo42ZNCRUs5rJsfQDma6Aw0DY=;
b=SO94qAGMgv7pY/8hGPmAvgN6YIOFtvl/x2iFJwN+BcUHh2zQ/ORo/WMq9osk/ErAO
f6DlsVSSDL5+6quGaywNHnt+vtHwA8RbT63URptTfrSpNuqRbqisBQiROQ4WZVU
Received: from Dell8700 (207-255-13-129-dhcp.jst.pa.atlanticbb.net) by mail.digitaliway.net with SMTP;
Wed, 2 Sep 2015 07:55:36 -0400
From: "Mike Danchanko" <REDACTED@digitaliway.com>
To: <support@chicagonettech.com>
Subject: SMTP ALT
Date: Wed, 2 Sep 2015 07:55:46 -0400
Message-ID: <008101d0e576$4e8735d0$eb95a170$@digitaliway.com>
MIME-Version: 1.0
Content-Type: multipart/mixed;
boundary="----=_NextPart_000_0082_01D0E554.C7760B00"
X-Mailer: Microsoft Outlook 15.0
Thread-Index: AdDldaSXZzDFHXXiSSOrF0GgcoY8kw==
Content-Language: en-us
[COMMENT: LOOKS LIKE YOU ARE USING DECLUDE]
X-MessageSniffer-Identifier: e:\SmarterMail\Spool\proc\work\49598016.eml
X-GBUdb-Analysis: Unknown
X-MessageSniffer-Scan-Result: 0
X-MessageSniffer-Rules: 0-0-0-32767-c
X-Declude-Spoolname: 49598016.eml
X-Declude-RefID:
X-Declude-Note: Scanned by Declude 4.12.11
X-Declude-Scan: Outgoing Score [0] at 07:55:44 on 02 Sep 2015
X-Declude-Tests: Whitelisted
X-Country-Chain:
X-Declude-Code: e
X-HELO: Dell8700
X-Identity: 0.0.0.0 | (Private IP) | chicagonettech.com <==== WHAT'S WITH THE "0.0.0.0" PRIVATE IP ADDRESS?
X-SmarterMail-Spam: SPF_Pass, DK_Pass, DKIM_Pass
X-SmarterMail-TotalSpamWeight: 0
It appears as if you might have DECLUDE enabled. How is that interfaced with SmarterMail, and why are you checking outgoing messages?