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Smarthost, SMTP Connector Help

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Smarthost, SMTP Connector Help - 19.Apr.2008 8:57:30 AM   
admintola

 

Posts: 3
Joined: 19.Apr.2008
Status: offline
I am trying to change the routing in my domain but messages fail to get delivered. What am I doing wrong?

Here is my setup:

1.Backend Server BE01 sends mail via SMTP Virtual Server to Smarthost for
Whitelisting
2. Smarthost forwards mail to Frontend Server FE01
3. FE01 sends to internet via SMTP Connector using DNS


Heres what I would Like to do:


Backend BE01 sends to Smarthost via SMTP Connector
Smarthost forwards mail to Frontend Server FE01
FE01 sends to internet via DNS
Add 2nd backend Server BE02 to use new SMTP Connector


This is what I setup:


I disable/stop SMTP Virtual Server on BE01
I add SMTP Connector to Routing Group to forward to Smarthost via [IP address]
I list BE01 as Bridgehead server in SMTP Connector


Result:

1. Messages are returned with You do not have permission to send to this recipient.  For assistance, contact your system administrator.
BE01.xxxxxx.com #5.7.1 smtp;550 5.7.1 Unable to relay for xxxxxxxxxxx


2. I then swap BE01 as Bridgehead with FE01 in SMTP connector and get the same error message:
You do not have permission to send to this recipient.  For assistance, contact your system administrator.
FE01.xxxxxx.com #5.7.1 smtp;550 5.7.1 Unable to relay for xxxxxxxxxxx


Could someone show me the errors of my ways.
 
Thanks



Post #: 1
RE: Smarthost, SMTP Connector Help - 24.Apr.2008 4:29:53 PM   
admintola

 

Posts: 3
Joined: 19.Apr.2008
Status: offline
Bump

Could anybody please give me some pointers here, I'm really stuck.

Thanks

(in reply to admintola)
Post #: 2
RE: Smarthost, SMTP Connector Help - 27.Apr.2008 7:15:41 PM   
Sembee

 

Posts: 4093
Joined: 17.Jan.2008
From: Somewhere near London, UK
Status: offline
First - you cannot stop SMTP virtual server on any Exchange server and expect that server to operate normally.
Second - you cannot send email out to another non-Exchange server then back in to the Exchange org for delivery.

It appears that you are trying to do the second, which will not happen.

Once a message has left the Exchange ORG, that is it. It can only go to an external SMTP server. Therefore if you want to send email through another server to whitelist it then that server must be the server that does the external delivery of email.

The only reason I can think that it may have worked in the past was by putting a smart host on the SMTP virtual server. While that will work with a single server deployment, it will not work with a multiple server deployment because Exchange servers communicate by SMTP and must communicate directly - inter-server traffic cannot go via another non-Exchange server.

Simon.

_____________________________

Simon Butler,
Exchange MVP
Blog: http://blog.sembee.co.uk/
Web: http://www.amset.info/
In the UK? Hire me: http://www.sembee.co.uk/
Exchange Resources: http://exbpa.com/

(in reply to admintola)
Post #: 3
RE: Smarthost, SMTP Connector Help - 28.Apr.2008 2:46:12 PM   
admintola

 

Posts: 3
Joined: 19.Apr.2008
Status: offline
Sembee,
 
thanks for the reply.
 
In the current setup between the backend server (BE01) and the Frontend box (FE01) is the Spam filter/whitelist box (ASSP). I know the Virtual Server on the backend box forwards to the Smarthost (ASSP) and this uses the Frontend box as it's relay to the Internet.
Maybe because the ASSP box acts as a proxy messages just pass through it to the frontend server. Messages on the internet show the Frontend box as the sending unit.
 
This has been working fine for over a year, I just want to add some redundancy to the setup hence the Connector issue/question.
 
Thanks

(in reply to Sembee)
Post #: 4
RE: Smarthost, SMTP Connector Help - 28.Apr.2008 3:12:51 PM   
Sembee

 

Posts: 4093
Joined: 17.Jan.2008
From: Somewhere near London, UK
Status: offline
Ah, the old "its worked for x" excuse.

The fact that something has worked in the past does not mean that it was the correct way to work or that it will continue to work in the future.

Basically what you were doing was not the correct way to deploy Exchange. You should never have anything between Exchange servers, they need to communicate directly. The fact that it appeared to work was more by luck - and only worked because you were using a single server.

The ASSP server should be the last server the messages go through and should be in front of all Exchange servers. Direct access to the OWA server for HTTPS access only.

If you want to introduce a second Exchange server for mailboxes you need to fix your broken deployment. That may seem harsh, but Exchange is designed to work in a specific way.

Simon.



_____________________________

Simon Butler,
Exchange MVP
Blog: http://blog.sembee.co.uk/
Web: http://www.amset.info/
In the UK? Hire me: http://www.sembee.co.uk/
Exchange Resources: http://exbpa.com/

(in reply to admintola)
Post #: 5

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