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Can not send email to Smart host

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Can not send email to Smart host - 21.Nov.2008 9:29:56 PM

drd

Posts: 20
Joined: 8.Aug.2008
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I configured the SMTP connector to smarthost to FQDN and even tried [IP address] in brackets. Once I click send I immediately receive undeliverable

The following recipient(s) could not be reached:
xyz@yahoo.com on 11/21/2008 9:12 PM
There was a SMTP communication problem with the recipient's email server. Please contact your system administrator.
<server.domain.com #5.5.0 smtp;504 >

Current configuration:
A few Exchange 2003 SP2 mailbox roles all using one client access server. Routing group connector each AD site and one SMTP connector to smart host.

The message never hits the smart host so it never leaves the front end server. No errors are in the event viewer and I have reviewed many articles. Can anyone assist me?

< Message edited by drd -- 24.Nov.2008 7:44:27 AM >

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RE: Can not send email to Smart host - 21.Nov.2008 11:42:24 PM

uemurad

Posts: 5571
Joined: 7.Jan.2004
From: California, USA
Status: online

Is the Smarthost you list in your connector your Front End server, an internal gateway or an external gateway? I'm trying to understand your configuration, but your description has me a bit confused.

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Dean T. Uemura
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(in reply to drd)

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RE: Can not send email to Smart host - 24.Nov.2008 7:44:01 AM

drd

Posts: 20
Joined: 8.Aug.2008
Status: offline

Thanks for your response. The smarthost is an external gateway.

The front end server points to the smarthost via smtp connector. However no emails are being delivered, it never leaves the front end server. .

< Message edited by drd -- 24.Nov.2008 8:04:58 AM >

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RE: Can not send email to Smart host - 24.Nov.2008 8:46:59 AM

de.blackman

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From: Toronto, Canada
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Are you able to successfully establish a telnet session (on port 25) and spoof a message to an external recipient from the front-end server to your smarthost?

Also does the smart host require any type of authentication?

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(in reply to drd)

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RE: Can not send email to Smart host - 24.Nov.2008 9:09:53 AM

drd

Posts: 20
Joined: 8.Aug.2008
Status: offline

Here is the results when I try to establish a telnet session

220 xyz.mydomain.com ESMTP ***** SMTP Ready *****
helo domain.com
250 xyz.domain.com
mail from:<myuser@mydomain.com>
504

Connection to host lost.

What is 504?

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Post #: 5

RE: Can not send email to Smart host - 24.Nov.2008 6:37:25 PM

uemurad

Posts: 5571
Joined: 7.Jan.2004
From: California, USA
Status: online

The external gateway is requiring you to authenticate before accepting the outbound message. First, verify that this is the case with whomever is responsible for the gateway, then check your settings within your SMTP Connector (Advanced tab, Outbound Security button).

_____________________________

Regards,

Dean T. Uemura
Microsoft MVP - Exchange
exchangeguy.blogspot.com
uemurad@yahoo.com

(in reply to drd)

Post #: 6

RE: Can not send email to Smart host - 25.Nov.2008 2:33:45 AM

NileshS

Posts: 67
Joined: 27.Apr.2008
Status: offline

504 basically means "Command parameter is not implemented".

It seems that there is some sort of authentication which is failing when trying to connect to your smarthost. Can you check by removing the smarthost and see if the mail goes through?

Check to make sure that all the default settings related to security (Advanced tab, Outbound Security button, Integrated authentication etc..) are in place.

How to troubleshoot the "504 need to authenticate first" SMTP protocol error
http://support.microsoft.com/?id=843106

< Message edited by NileshS -- 25.Nov.2008 2:35:04 AM >

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RE: Can not send email to Smart host - 25.Nov.2008 9:24:00 AM

drd

Posts: 20
Joined: 8.Aug.2008
Status: offline

My assumptions were right. It was a communication issue btw the front end to the smart host. Our network engineer made some changes to the routes/configuration and as is well.

I can send successfully through the smart host.

(in reply to NileshS)

Post #: 8