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Microsoft Exchange Server 2003 - "The SMTP Trible-Trouble Receipient Maze"

Hello Community-

Have really major issue on hands right now.  Did a SBS2003 with Microsoft Exchange 2003, SP2 on the weekend.
All looked OK.
However, big problem.  Sending to remote based staff using external domain name not working.  

Context:  There are about 7 internal people based in an office and with an account in Exchange, Active Directory.  These folks can communicate with themselves.  So OK.

The Problem: However, there are remotely based individuals who do not have a mailbox on the local exchange server, nor AD account, but only the Internet-based POP3 account.  

The POP3 receiving mail is OK for internal users.  And for external.  Sending between each other is the problem. Buthen an internal user (with Exchange mailbox) tries to contact remotely based staff member with no exchange account (but same internet domain name), the following happens:
"1"
  The e-mail account does not exist at the organization this message was sent to. Check the e-mail address, or contact the recipient directly to find out the correct address.

"2"
If I create the remotley basd user account on the local exchange server, mail only makes it to the internal mailbox, never to go outside to the POP3 mailbox.  So above error bypassed, but mail just stays inside organisation...but I need it to go outside, however, the exchange server's domain name is the same as internet domain name...so email stays local.  Not good.

"3"
Even if I create a external contact for the remote user, the following appears:
A configuration error in the e-mail system caused the message to bounce between two servers or to be forwarded between two recipients. Contact your administrator.

Not sure how to proceed.   Any ideas, very, very appreciated.
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ASKER

I just thought of a way of saying the above in 10 words:

"external recipients with the same e-mail domain as internal staff"
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This is pretty common, and there is a good way, and a bad way to fix it.

The good way is to get your server receiving mail directly, doing away with the atrocious pop3 connector, and have external users access email using RPC/HTTP.

The bad way, which is acceptable very briefly until you implement the above, is to route all email with unknown recipients back to the ISPs mailserver;

Open ESM, drill down to the SMTP virtual server, right click, properties, go to the messages tab, down the bottom is a "Forward all mail with unresolved recipients to host" box, put in "mail.isp.com" or wherever you are downloading mail from.

So, what will happen now is all internal users will send mail to external users, exchange will know they don't exist and fling the mail back to the ISP, which will put it where it needs to go.  Be warned - bad things can happen with typo's causing all kinds of duplication - the best way to do it is what I indicated first.

Good luck

Kieran
Hi Kieran -  Thank you.

I have found this:
"E-mail to external recipients with the same e-mail domain causes NDR messages when using the POP3 Connector" - http://support.microsoft.com/kb/300681 

In order to do the above.. the following is a pre-requiste from :
-->The SMTP mail server that is specified must be the ISP mail server that receives messages for the POP3 accounts.  

In my case the POP3 server which recieves mail is different from the one from which I download email.  Trying to find which mailbox receives mail is not easy for me.

Thus I followed method 2 above.  Very odd. Some work, Some don't.  One person cannot mail one other, but she can email others, even though they are not Active Directory mailboxes but go outside to the internet DNS domain name.


To find out which server receives mail for the pop3 accounts, put your domain in here -> http://www.zmailer.org/mxverify.html

It will come up with a few servers in the MX records - just add any of those in there.

I still think you should consider doing this without the POP3 connector - it is not meant as a long term solution.
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