Take the 2-minute tour ×
Server Fault is a question and answer site for professional system and network administrators. It's 100% free, no registration required.

I have a very bizarre set of circumstances. One of my staff received an e-mail addressed to me from a consultant, however this consultant would have no idea who this staff is or their e-mail address. I also received the e-mail, however it's quite concerning to me that something like this might happen.

Points worth noting

  • The anti-spam logs do NOT show my colleague getting the mail, but show me getting the mail.
  • The Exchange Tracking Logs show both of us getting it (they are bizarre though - more on that below)
  • This is a lone exchange server that serves CAS, HT and MB roles
  • Server is up-to-date with updates and service packs
  • Spam filtering is done with Exchange Server Toolbox V4
  • There are no delegate permissions or forwarding rules on either of our accounts

Below is the scrubbed message tracking log - the peculiar thing is that I am the correct recipient, however that e-mail arrives one minute after the incorrect. You'll also note that the two Client IP's, Client Hostnames, Server hostnames and return paths are completely different - as if they've come from two different people.

Timestamp   ClientIp    ClientHostname  ServerIp    ServerHostname  SourceContext   EventId InternalMessageId   MessageId   TotalBytes  RecipientCount  MessageSubject  Sender  ReturnPath
07/09/2013 11:40    2.2.2.2 different.sending.server.com    10.0.0.7    postmaster  08D04A67B764B4DB;2013-07-09T15:40:26.336Z;0 RECEIVE 253201  <6FC8422858D3E0419323DB54F887D2CC390F0BF9@mbx023-w1-ca-10.exch023.domain.local> 8882    1   RE: Server Down?    sender@domain.com   wrongemail@differentdomain.com
07/09/2013 11:40        myserver        MYSERVER    08D04A67B764B4E9;2013-07-09T15:40:54.377Z;0 DELIVER 253201  <6FC8422858D3E0419323DB54F887D2CC390F0BF9@mbx023-w1-ca-10.exch023.domain.local> 9212    1   RE: Server Down?    sender@domain.com   wrongemail@differentdomain.com
07/09/2013 11:41    1.1.1.1 correct.sending.server.com  10.0.0.7    postmaster  08D04A67B764B4E2;2013-07-09T15:40:42.088Z;0 RECEIVE 253207  <6FC8422858D3E0419323DB54F887D2CC390F0BF9@mbx023-w1-ca-10.exch023.domain.local> 9437    1   RE: Server Down?    sender@domain.com   sender@domain.com
07/09/2013 11:41        myserver        MYSERVER    08D04A67B764B4EF;2013-07-09T15:41:18.790Z;0 DELIVER 253207  <6FC8422858D3E0419323DB54F887D2CC390F0BF9@mbx023-w1-ca-10.exch023.domain.local> 9767    1   RE: Server Down?    sender@domain.com   sender@domain.com

Does anyone know what might cause this??

EDIT : Sanitized logs of e-mail sent to my colleague

X-Process: ESTProcessDone
Received: from hub023-ca-3.exch023.serverdata.net (1.1.1.1) by
myserver.mydomain.com (10.0.0.7) with Microsoft SMTP Server (TLS) id
14.3.123.3; Tue, 9 Jul 2013 11:40:42 -0400
Received: from MBX023-W1-CA-10.exch023.domain.local ([10.254.8.60]) by
HUB023-CA-3.exch023.domain.local ([10.254.8.36]) with mapi id 14.03.0123.003;
Tue, 9 Jul 2013 08:40:41 -0700
From: sender <sender@domain.com>
To: Me <me@mydomain.com>
Subject: RE: Server Down?
Thread-Topic: Server Down?
Thread-Index: Ac58tY3CMo8EMLUTR3OVT6VTqv9MowAApWDwAACb9EA=
Date: Tue, 9 Jul 2013 15:40:41 +0000
Message-ID: <6FC8422858D3E0419323DB54F887D2CC390F0BF9@mbx023-w1-ca-10.exch023.domain.local>
References: <6FC8422858D3E0419323DB54F887D2CC390F0B9B@mbx023-w1-ca-10.exch023.domain.local>
<DA59270178440942B362BC622B47E790036E3E4C@myserver.mydomain.com>
In-Reply-To: <DA59270178440942B362BC622B47E790036E3E4C@myserver.mydomain.com>
Accept-Language: en-US
Content-Language: en-US
X-MS-Has-Attach:
X-MS-TNEF-Correlator:
x-originating-ip: [3.3.3.3]
Content-Type: multipart/alternative;
                boundary="_000_6FC8422858D3E0419323DB54F887D2CC390F0BF9mbx023w1ca10exc_"
MIME-Version: 1.0
Return-Path: sender@domain.com
X-MS-Exchange-Organization-AuthSource: myserver.mydomain.com
X-MS-Exchange-Organization-AuthAs: Anonymous

EDIT 2 :

After reviewing the anti-spam logs it looks as though my colleague had an e-mail arrive to her at the exact time the incorrect one was delivered to her. The aforementioned e-mail is from the same person / IP address that shows up in "different.sending.server" and "2.2.2.2" Client IP Address.

My colleague never received the e-mail listed above but instead received the one addressed to me.

share|improve this question
    
Could you provide sanitized internet headers for either of the incorrectly delivered messages? –  Jeremy Lyons Jul 10 '13 at 2:37
    
@JeremyLyons Updated with sanitized headers of incorrectly delivered message –  DKNUCKLES Jul 10 '13 at 14:39

2 Answers 2

Occam's Razor: The sender "BCC'd" your co-worker when they emailed you. You don't recall receiving the one sent to yourself.

share|improve this answer
up vote 1 down vote accepted

After some very thorough investigation I think I can safely say that we isolated the problem to the anti-spam (Exchange Server Toolbox). The software has been updated and other weird issues that we had experienced with our server seem to have resolved themselves as well.

share|improve this answer

Your Answer

 
discard

By posting your answer, you agree to the privacy policy and terms of service.

Not the answer you're looking for? Browse other questions tagged or ask your own question.