troubleshooting Question

Help Analyzing Email Header Information

Avatar of jmerulla
jmerullaFlag for United States of America asked on
Email Protocols
10 Comments2 Solutions2175 ViewsLast Modified:
Help.  I'm looking for a reality check here and was hoping you can help.  

We are working with a vendor that swears the following emails are being set to us encrypted and secure (it's confidential information that cannot be sent via Normal smpt traffic).   But the way I'm reading the header information, it looks like it was sent via normal smtp.

We use Postini as our spam filter, and do have a TLS route between Postini & My Mail Server.

smtp2.VENDOR-NetworkID.com resolves to VENDOR-IP-ADDRESS

It looks like based on this line that the mail is traveling via SMTP from the vendor to Postini.  

Received: from source ([VENDOR-IP-ADDRESS]) by exprodXXX.postini.com ([POSTINI-IP-ADDRESS]) with SMTP;

It looks like maybe there are secured hops but that main one to our Postini is unencrypted.


------------------------------------------------------------------

Microsoft Mail Internet Headers Version 2.0
Received: from psmtp.com ([MY-INTERNAL-SERVER-IP] RDNS failed) by MY-SERVER-NAME over TLS secured channel with Microsoft SMTPSVC(6.0.3790.4675);
       Tue, 27 Jul 2010 09:02:41 -0400
Received: from source ([VENDOR-IP-ADDRESS]) by exprodXXX.postini.com ([POSTINI-IP-ADDRESS]) with SMTP;
      Tue, 27 Jul 2010 08:02:39 CDT
X-IronPort-AV: E=Sophos;i="4.55,267,1278302400";
   d="pdf'?scan'208";a="73036257"
Received: from unknown (HELO LLLLLL.corpads.local) ([10.xx.xx.xxx])
  by smtp2.VENDOR-NetworkID.com with ESMTP; 27 Jul 2010 09:01:01 -0400
Received: from 10.xx.x.xxx by LLLLLL.corpads.local with ESMTP (Secure
 Mail SMTP Relay (Email Firewall v6.3.0)); Tue, 27 Jul 2010 09:02:26
 -0400

X-Server-Uuid: Cmmmmmmm-mmmmmmm-mmmm-mmmmmmmmmm
To: reciepients
cc: Carbons
MIME-Version: 1.0
Subject: Subject
X-KeepSent: 000000:00000:000000; type=4; name=$KeepSent
X-Mailer: Lotus Notes Release 8.0.2 August 07, 2008
Message-ID: <Cmmmmmmm-mmmmmmm-mmmm-mmmmmmmmmm@VENDOR.com>
From: sENDER
Date: Tue, 27 Jul 2010 09:02:20 -0400
X-MIMETrack: S/MIME Sign by Notes Client on sENDER-NAME
 (Release 8.0.2|August 07, 2008) at 07/27/2010 09:02:23
 AM, Serialize by Notes Client on MsENDER-NAME(Release
 8.0.2|August 07, 2008) at 07/27/2010 09:02:23 AM, Serialize complete at
 07/27/2010 09:02:23 AM, S/MIME Sign failed at 07/27/2010 09:02:23 AM:
 The cryptographic key was not found, Serialize by Router on
 VENDORM09/VENDOR(Release 8.0.2|August 07, 2008) at 07/27/2010 09:02:36
 AM
X-WSS-ID: 605007680Z0364924-01-03
Content-Type: multipart/mixed;
 boundary="=_mixed 0047A1598525776D_="
X-CFilter-Loop: Reflected
X-pstn-neptune: 0/0/0.00/0
X-pstn-levels:     (S:00.00000/00.00000 CV:99.9000 FC:00.0000 LC:00.0000 R:00.0000 P:00.0000 M:00.0000 C:00.0000 )
Return-Path: SENDER EMAIL
X-OriginalArrivalTime: 27 Jul 2010 13:02:41.0672 (UTC) FILETIME=[fffffff:000000]

--=_mixed 00000000000000000000_=
Content-Type: multipart/alternative;
 boundary="=_alternative 0047A1598525776D_="
Content-Transfer-Encoding: 7bit

--=_alternative 00000000000000000000_=
Content-Type: text/plain;
 charset=us-ascii
Content-Transfer-Encoding: 7bit

--=_alternative 00000000000000000000_=
Content-Type: text/html;
 charset=us-ascii
Content-Transfer-Encoding: 7bit


--=_alternative 00000000000000000000_=--
--=_mixed 000000000000000000000_=
Content-Type: application/octet-stream;
 name="ATTACHEMENTNAME.PDF"
Content-Disposition: attachment;
 filename="ATTACHEMENTNAME.PDF"
Content-Transfer-Encoding: base64


--=_mixed 00000000000000000000_=--
ASKER CERTIFIED SOLUTION
KNolen

Our community of experts have been thoroughly vetted for their expertise and industry experience.

Join our community to see this answer!
Unlock 2 Answers and 10 Comments.
Start Free Trial
Learn from the best

Network and collaborate with thousands of CTOs, CISOs, and IT Pros rooting for you and your success.

Andrew Hancock - VMware vExpert
See if this solution works for you by signing up for a 7 day free trial.
Unlock 2 Answers and 10 Comments.
Try for 7 days

”The time we save is the biggest benefit of E-E to our team. What could take multiple guys 2 hours or more each to find is accessed in around 15 minutes on Experts Exchange.

-Mike Kapnisakis, Warner Bros