"We do not relay" NDR, happens sporatically (1 in 20?) and only for replies

This is my first time setting up an Exchange server (2003 SP1) to receive POP3 email, so please bear with me... the problem is that while replying some of the messages are returned with a System Administrator message stating:

You do not have permission to send to this recipient. For assistance, contact your system administrator.

<xxxx.org #5.7.1 smtp;550 5.7.1 <username@zzzz.com>... we do not relay <user@xxxx.org>>

Yet, sometimes the messages to "username@zzzz.com" will go through just fine. I cannot predictably replicate the problem. The users are sending all email via Outlook 2003.

Here is the setup:
- The server's OS is Windows Small Business Server 2003 Standard Edition.
- All 3 client computers are set up to send and receive email from their website/email host (halfpricehosting.com). All of their profile info (email, calendar, tasks, etc) is being stored in their Exchange mailbox. Most of the time everything functions normally, except as noted above. All computers are using Outlook 2003 and are located on the same domain as the Exchange server, thus they should be able to relay via authenication(?).
- When sending email via Outlook Web Access they always receive the "we do not relay" NDR... Otherwise, OWA correctly displays their mailbox/profile info.
- POP3 connector is configured and seems to be working correctly.
- In the default recipient policy "@xxxx.org" is selected as the primary address.
- Ports 110 and 25 are forwarding to Exchange server IP.

Please let me know if you need more info! Thanks!

-Shamus J Daily
shammydAsked:
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SembeeCommented:
It appears that you didn't quite understand my question regarding DNS.
In the properties of TCP/IP, under DNS is the server the only listed DNS server? It should have its own IP address listed.

I think SBS does setup an SMTP Connector. You can find them in ESM, Admin Groups, <your admin group>, Routing Groups <your routing group> - or something very similar.

Simon.
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SembeeCommented:
I think the "we do not relay" message from OWA is the pointer in this issue. When email is sent via OWA it isn't relaying, it is coming straight from the server. Get that problem resolved and I think the others will be fixed.

First instinct is DNS.
Is the Exchange server using ONLY internal DNS servers in the configuration of the DNS for Windows?
Are you using any kind of Smart Host information, or SMTP Connectors?
I presume that "xxxx.org" was your Exchange server? Was it in the format name.com or was it host.name.com?

Simon.
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shammydAuthor Commented:
Thanks for the comments...

I completely agree with you; if I fix the OWA, the others will follow.

Let me answer your DNS questions:
- Yes, the only DNS server on the domain is the same box as the Exchange server (Windows Small Business Server 2003).
- We are not using any Smart Host information or SMTP Connectors, at least that I am aware of. Give me an example...
- The name of the server is in the form of computername.domain.org.

Thanks!
-Shamus
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shammydAuthor Commented:
Sorry for the misunderstanding...

The only IP address that appears in the DNS list under TCP/IP is the server's IP address (192.168.2.25). There is no secondary address.

Last night I discovered that SBS does use an SMTP Connector. Thank you...

I fixed most of my own problem late last night. Sending email from OWA still doesn't work, but my client isn't receiving anymore NDRs when sending from Outlook. They don't mind using Remote Web Workplace to get to their desktops and then accessing Outloook from there, so my problem is "fixed". Here is the Microsoft KB file that helped me with some of the configurations:

http://support.microsoft.com/default.aspx?scid=kb;en-us;Q319759

Now, if you (or anyone) can figure out how to get OWA to be able to send email, that would be really great!

Thanks again!
-Shamus
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