Exchange 2003 SP2 problem when sending mail not directly but via external mail server ...

Posted on 2006-10-24
Last Modified: 2010-03-06
Hello. I have successfully configured my (in SBS2003 R2) Exchange 2003 SP2 to successfully send all emails via an external (authenticated) email relay called Previously, I had been sending emai 'direct' via DNS from Exchange, but this has been leading to occasional rejections from recipient servers who didn't mind our email address but hated our sending server (my Exchange) because it was coming from a dynamic IP address and they didn't trust it.
So I reconfigured it as per the following previous question;

by re-running the Internet and Email Wizard.

All seems fine as emails clearly go through AUTHSMTP (as one can see from their control panel logs).

***** BUT ******* an interesting glitch has come up! Previously one of my user accounts had been forwarding directly to her Blackberry t-mobile acount. This worked fine. But now that ALL emails go through and they ONLY allow a certain number of authenticated email addresses to to relay through them, this blackberry forwarding stops working as from the point of view of, an email from (say) I have forwarded to my users Blackberry is not an allowed email address (because it's not from me but from, and thus they won't onward relay it!!!

Any solution to this? Is there a way of making an exception on the connector?
Question by:MPSmith4258
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Accepted Solution

dynamitedotorg earned 500 total points
ID: 17801753
Add a new connector, tell it to use DNS to deliver, then under Address Space put the domain of this particular external email address with a cost of 1.

You might need to increase the "cost" of your existing connector to something higher than 1 in order to allow this mail to go out via the correct connector.
LVL 39

Expert Comment

ID: 17802269
Hi MPSmith4258,

That isn't going to work - you would need to add every domain into that new connector, making it quite useless.

Are you using BES for this at all?  If not, that is where I would be looking next.

The Express version is free for 1 client ->

Hope that helps,


Expert Comment

ID: 17802321
I think your misreading what I wrote, or more likely I didn't write what I actually meant :)

You'd put the DESTINATION domain in address space for the connector. That way mail to that particular t-mobile account that the user is forwarding to will go direct, everything else will go via Authsmtp.
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Author Comment

ID: 17804295
Hi there, tried the new SMTP connector - set it up to DNS with an address space of just, and a cost of 1, all other entries were left at default. I did then alter the existing default connector to have a cost of 2 (and it has an address space of *) but of course left everything else as it was.

From my point of view, outgoing email should be checked through the new connector. If the outbound email is to the same domain as in the address space, then its sent (via DNS) through that connector. If not, then the next connector in line (the previous default) is used.

Unfortunately, that does not seem to happen. I've checked I've done it ok. All emails to * still go through the old connector, with the problems that ensue from that. I've run gpupdate /force, and even stopped and restarted the SMTP Virtual Server, all to no affect.

Any more ideas gratefully rec'd!

Author Comment

ID: 17804302
Oh and Blackberry Enterprise Server looks a little daunting from an installation point view. Is it more straightforward than it looks?
LVL 39

Expert Comment

ID: 17807470
Short answer, no, it isn't simple.

My memories of doing it were a bit of a nightmare.  Although, once configured it is stable, and I would definitely do it again :)

Just don't put it on your exchange server and you should be all right - old desktops do this really well.

My main problem was not reading the instructions (which is always a last resort for me) so following them will probably make it far easier :))

LVL 39

Expert Comment

ID: 17807487
Oh, and I was installing full blown BES, the express edition is probably much easier anyway.

And I understand what you mean now dynamite :)

Author Comment

ID: 17815204
Dynamite, have tried your solution again, more carefully read the Microsoft Knowledge Base article on it too ... the reason is following creation of a new connector, the SMTP service AND the Routing Engine need to be restarted; now works perfectly, all email to the * domain goes via DNS, the rest via the more trustworthy authsmtp authenticated relay service.

Many thanks to you both. RedSeat, I think I'll pass on the Blackberry server approach. There are other non blackberry people I will need to forward to in the future, so I def needed a native Exchange solution.

Incidentally, I trialled a Sperry forwarding addin as a temp workround. Worked fine apart from the fact that it's a client side solution!

Regards to you both.

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