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Message sent to external recipient also delivers a copy of the message to local sender

Posted on 2006-06-27
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Last Modified: 2013-11-15
I have an Exchange 2003 standard server running on a simle and small AD network.  When a single user on the system sends a message to some external recipients, the message sent also gets delivered to the senders local exchange mailbox.  It doesn't happen with every external recipient, but with several recipients.  Most of which have email addresses ending in verizon.net.  I can't find any exchange settings or AD profile options that would account for this user receiving an actual copy of the message they are trying to send to an external recipient.  Here is what is happening step by step

1. user composes an email to an external recipient, outside of the exchange org (which AD and Exchange had generic internal names)
2. User types message and verifies that only this one recipient is selected to receive the message in the "To" field.  
3. user hits send, and the message sends through outlook...

Now if I look in message tracking I can see where the queue actually queues the mail twice, it goes through the categorizer and gets routed for external delivery, but then it starts over and goes back through the queue and this time appends with being delivered locally to the senders address.  The last line shows the message getting sent via SMTP externally, so the recipient still gets the message, but the sender gets a copy too, even though the sender did not send the message to himself.  

Does this make any sense to anyone, where would I begin to troubleshoot this?  I've already checked all through my exchange server settings and AD user properties for the mailbox, I don't see anything wrong or anything that would explain why this is happening, I can only tell that it is happening and the message tracking center that its queuing twice.  Again, this does not happen for every recipient this sender sends mail to.  Very puzzling.  You can see a screenshot of the message tracking center at http://www.shorehost.com/Message.jpg which shows the message getting queued twice.  

I tried sending a message to this same recipient from my mailbox and did NOT receive a copy back to myself.  So its just something with this one mailbox.  The message tracking center only had half the content of the screenshot for the instance of when I sent the message, showing only a single delivery.

Thanks


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Question by:MCPJoe
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by:MCPJoe
ID: 16997347
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by:mvvinod
ID: 16998300
1. Check to see rules that exist on user's outlook. See if any rule is causing this..
2. Find a external address that you can consistently check...Eg. is there one e-mail address that will always send to external user and local user also ???

Vinod.
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by:MCPJoe
ID: 17000287
1. user has no outlook rules
2. Its always to any user @verizon.net but only this domain, external mail sent to any other address is fine.

Its driving me crazy that I can't figure this one out.  It doesn't make any sense.  
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by:mvvinod
ID: 17001075
Have you tried extracting the user's mailbox through exmerge, deleting the mailbox, purging it, recreating the mailbox and put the mails back on ???

Vinod.
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by:MCPJoe
ID: 17001099
That was my last resort step.  I am going to try to upgrade the server to Enterprise edition anyway, so I may just wait until after the upgrade and see if its still a problem.  If so, I guess I don't have any other options.  Its just really weird that its only for verizon.net accounts.  
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by:mvvinod
ID: 17001184
Yeah...really strange....

Have you checked the sent items to see if more than 1 recipient exist is to,cc or bcc ??

Vinod.
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by:mvvinod
ID: 17001199
For the same user, when you use Outlook Web Access, does the same thing happen???

Vinod.

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by:MCPJoe
ID: 17001213
Yes, and it only shows the senders address and the recipients address.  No where in outlook, or in the message properties, or in the exchange server settings do I see anything indicating a reason why the server is delivering a local copy of all messages sent to verizon.net addresses to the sender.  And even more strange is that its just from this one mailbox, from my mailbox it works fine, but with the other mailbox, it gets the duplicate message delivery.  My exchange server is using a smarthost to send outgoing SMTP mail, but this is the first time I've had a problem like this with it.

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by:MCPJoe
ID: 17001222
Yes, same issue occurs when using OWA
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by:Sembee
ID: 17002910
What does message tracking show?
Did the message go out and come back in again? SMTP headers will tell you that.

Simon.
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by:MCPJoe
ID: 17003794
nothing useful, message tracking shows whats in the screenshot I posted the link to.  Headers just show message coming to sender.
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by:Sembee
ID: 17003872
The headers should show you which server the message came from. That is the server that needs to be looked at.

Simon.
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by:MCPJoe
ID: 17059845
I only have this problem on one server, its not setup to copy messages to a recipient or group, its only configuration is to use a smarthost for outbount SMTP traffic.  At first I thought the problem might be with the verizon mail server, but after doing some tests, and sending some test messages, I found that immediately after hitting send on a message to a verizon.net recipient, the message would get delivered to the sender.  If it were an outside server, there would be at least a small delay before getting the message back, but there is no delay, its immediate.  This tells me its something on my server, but I can't figure out what.  I don't have verizon.net in my internal DNS used by this exchange server, and I'm using my ISP dns for forwarders in internal DNS.  Like I said, the only configuration change I made was to use a smart host.  I could try to remove the smarthost settings but this will cause a problem sending to verizon as my public IP on the network my exchange server is on, happens to be on some kind of blacklist with verizon, so they block all mail that is sent directly from my Exchange server.  I am going to try another smarthose provider and see if it helps, but I doubt it.  I don't know what else I can check.  
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by:Sembee
ID: 17060129
Does the copy of the message that is received by the user have SMTP headers? That will prove whether the message has been through the SMTP engine or not. If there are headers, do they show any external servers at all?

Simon.
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by:MCPJoe
ID: 17233134
Here are the headers...
_____
Microsoft Mail Internet Headers Version 2.0

Received: from mail pickup service by starbuck.XXXXXXXX.com with Microsoft SMTPSVC;

                 Tue, 1 Aug 2006 22:09:33 -0400

X-MimeOLE: Produced By Microsoft MimeOLE V6.00.3790.2663

Content-Transfer-Encoding: 7bit

Content-Class: urn:content-classes:message

Subject: RE: postcard

Importance: normal

Priority: normal

MIME-Version: 1.0

Content-Type: multipart/mixed;

                boundary="----_=_NextPart_001_01C6B5D8.B17EC52E"

Date: Tue, 1 Aug 2006 22:09:32 -0400

Message-ID: <C1BBFC7B4D8E24449FAC7D6E0C0FB57C061C72@starbuck.home.us>

X-MS-Has-Attach:

X-MS-TNEF-Correlator:

Thread-Topic: postcard

thread-index: Aca1xJgXsF+OoPDNRlKcLUsZCPMfSwAE/RHw

References: <C1BBFC7B4D8E24449FAC7D6E0C0FB57C061C70@XXXXXXX.us> <001801c6b5c4$92920b60$6600a8c0@FamilyRoom>

From: "Liz XXX" <Liz@XXXXX.us>

To: "The Home E-mail" <XXX@verizon.net>

X-OriginalArrivalTime: 02 Aug 2006 02:09:33.0692 (UTC) FILETIME=[B26143C0:01C6B5D8]


I changed the doamins to protect privacy, but any mail this user sends to verizon.net addresses gets copied back to her inbox.  It does not do this when I send from my mailbox on the same server.  I checked the users AD account, exchange properties, even checked for hidden attributes in ADSI Edit, but no strange or different settings at all, same as my mailbox.  There are no strange settings in her outlook profile either, I even tried creating a new exchange profile in outlook, but she still gets the duplicate message in her mailbox.  I have spent hours looking into this and just can't figure out whats causing it.  

I run GFI Mail Essentials and GFI mail security on this server, and thats it, no configuration in that software would cause this issue, I checked the logs and they don't show any sign of a duplicate delivery when this user sends mail, only shows the single instance of sending in the logs.  In Exchange message tracking center, the sent message goes through the normal routes and goes through the categorizor and queue, then starts over and does it again at the end showing local delivery to the sender and then it routes out through my smarthose to the internet for delivery to the original recipient.  This is very strange, and I also noticed that the sent message is being picked up by the pickup server, not SMTP directly.  Not sure why.  

Anyone have any ideas?

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Sembee earned 500 total points
ID: 17234252
Is there a POP3 connector involved? That can show the pickup service.

Otherwise I would probably suspect the GFI products. That is based on past experience with their stuff.

Simon.
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by:MCPJoe
ID: 17234293
GFI has a pop3 downloaded built into their mailessentials software, but it downloads mail for another external account to the local exchange mailbox, with different email addresses.  I can't understand why this issue only happens for verizon.net addresses...
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by:Sembee
ID: 17234951
If there is a POP3 connector involved, then I would suggest disabling it and see if the problem continues. If it does, then you know that the POP3 connector isn't the source of the problem.

Simon.
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by:MCPJoe
ID: 17241938
I thought it was Exchange doing something weird, I did hours of troubleshooting and checking around looking for the cause of the problem.  I ran tets and sent dozens of test email messages.  I almost got to the point where I was ready to delete her exchange mailbox and re-create it.  Well after all this time, the problem is finally fixed!!!  What was it you say?  Ha ha, well here is what happened....

   I use GFI Mail essentials as a spam filter on my server that has lots of cool options and advanced features and a bunch of extra stuff.  One day when I was first setting up the spam filter, I started playing around with mail monitoring rules.  Don't ask me why, but I had setup a test rule that had the conditions configured to copy this user on any outgoing message sent to verizon.net addresses.  I looked at that and could not believe it.  I completely forgot about setting that up and it never even occurred to me that the spam filter could be causing it.  I had checked every other option in the configuration and simply ignored the rule settings.  So now I deleted that stupid rule and what do you know, no more copied messages!  

   Sometimes in I.T. you encounter things that don't make any sense.  I thought I had discovered some new bug in Exchange or was having issues with my smarthost or something along those lines.  I was relieved to find that the problem was totally mine and had to laugh out loud.  But ahhhh, another problem solved!
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