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Problem setting up Exchange 2003 Smart Host

Posted on 2010-01-07
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Last Modified: 2012-05-08
I am trying to setup a client's Exchange 2003 single instance server, to use a Smart Host to send e-mail out to the internet through our filtering appliance.

I have my devices setup for opportunistic TLS for incoming connections.  I created a SMTP Connector on the Exchange 2003 box (didn't use default VS because I wanted to use two smarthosts and I think the VS only accepts one).  I used FQDN for our smarthosts, set everything correctly as I thought and then restarted the necessary services.

On my side, here is what I see in the log files...

Connect from mail.server.net (ip x.x.x.x)
setting up TLS connection from mail.server.net (ip x.x.x.x)
TLS connection established from from mail.server.net (ip x.x.x.x) TLSv1 with cipher RC4-MDF (128/128 bits)

******at this point I have to assume their server connected to mine without problem, using TLS******

Next lines....

NOQUEUE: reject: RCPT from from mail.server.net (ip x.x.x.x):  454 4.7.1 (email address) relay access denied from <> to (email address)

I'm guessing they aren't accepting incoming TLS on their side but not really sure.  any help is appreciated.  This is Exchange 2003 running on SBS2003
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Question by:rosederekj
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by:Wonko_the_Sane
ID: 26204639
I would say your filtering device doesn't allow relaying from their server - which would be expected if this is not an open relay.

Basically you will have to allow relaying from this Exchange server's IP and you should be fine ( from mail.server.net (ip x.x.x.x)  )
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by:rosederekj
ID: 26209442
Any additional insight on the 454 4.7.1 codes?  I'm wondering if there is something on their perimiter network causing the problem
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Wonko_the_Sane earned 2000 total points
ID: 26209595
Not sure... My guess is that your appliance doesn't like the connection from the server, either because it's not authenticating properly, it's not authenticating at all or because it doesn't allow relaying. The error says it's a relaying problem, but the 454 is technically TLS related.

It ultimately depends on the configuration of the appliance. Any chance you can see if it requires authentication to allow relaying? Or if you can allow relaying for unauthenticated hosts (make sure you only allow it for their IP)? Once you know this you can look into how to setup the smart host.

If you can, try doing it without TLS for the test - just to narrow it down more.
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Author Closing Comment

by:rosederekj
ID: 31674261
It did end up being a relay setting on the encryption devices - got that adjusted and everything works now.  Thanks!
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