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Problem sending mail between Exchange 2003 Server in the same organization/AD domain

Posted on 2005-04-04
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Last Modified: 2012-05-05
I have recently setup an exchange 2003 organization that have 3  exchange members in it:

mail01 (first exchange server/master) , mail02 and mail03.

However, i faced mail delivery problem between users in mail01 to users located in mail02  and mail03.

To diagnose the problem i ran some e-mail delivery test and here is the result.

sending e-mail:

from mail02 to internet mail address(eg. yahoo.com) - OK

from mail02 to mail01 - OK

from mail02 to mail02 - OK

from internet mail address(eg. yahoo.com) to mail01 - OK

from internet mail address(eg. yahoo.com) to mail02 - NOT OK stucked at mail01 queue -

mail02 folder

from internet mail address(eg. yahoo.com) to mail03 - NOT OK stucked at mail01 queue -

mail03 folder

from mail01 to mail02 - NOT OK stucked at mail01 queue - mail02 folder

from mail01 to mail03 - NOT OK stucked at mail01 queue - mail03 folder

from mail02 to mail03 - OK

from mail03 to mail02 - OK

FYI, all exchange servers except for mail02 is using public IP. Mail02 is using internal IP

but i don't think it is a problem as sending mail between mail02 and mail03 have proved to be successful. The only thing that is bugging me is why sending e-mail from yahoo and from user in mail01 failed if the recipient is located in mail02 and mail03 server.

Please give some insights and enligtenments on how to solve the problems. Any help and ideas is much appreciated.

TQ
-syahrul-
 
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Question by:nitrous_orangez
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Expert Comment

by:Sembee
ID: 13696700
We do have a dedicated Exchange Topic Area where this may have been picked up quicker.
http://www.experts-exchange.com/Networking/Email_Groupware/Exchange_Server/

Anyway...

Standard tests first.

From each server, attempt to connect to the other two servers using telnet to port 25:

telnet servername 25

See if you get a connection.
Repeat using the IP address and FQDN:

telnet 123.123.123.123 25

telnet servername.domain.com

Messages stuck in the queue is a classic connectivity issue.
Are you using any Smart Hosts ?

Simon.
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Author Comment

by:nitrous_orangez
ID: 13697584
All servers are able to telnet to each other on port 25 using servername, IP no as well as FQDN.

There are no smarthost defined on each of the server's default SMTP virtual server. However, I do put an IP of an external DNS as smarthost entry for my Internet Mail SMTP connector on my mail01 server. Also, I defined all exchange server ( mail01, mail02 and mail03) as local bridgeheads for the connector.

Is there anything wrong with my current settings? Please point me to the right direction..

syahrul
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Expert Comment

by:Sembee
ID: 13701052
That confirms that the connectivity is there...

As a test, try removing the SMTP Connector. Exchange can deliver email directly on its own, and it will not harm for a few minutes.
Any routing groups or other stuff like that setup?

Simon.
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Author Comment

by:nitrous_orangez
ID: 13703509
It is a pretty standard configuration, there are no routing groups configured, all servers are sitting in the same routing group from the beginning.

I would like to highlight though that there is a PIX firewall sitting between mail01 and mail02 network. Could this contribute to the problem i'm facing here?
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Expert Comment

by:Sembee
ID: 13705956
The barrier could be an issue.

Can you administrate both servers from the other using ESM?

Have you got the FIXUP SMTP option disabled on the PIX?

Simon.
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Author Comment

by:nitrous_orangez
ID: 13707346
I have no problems administering both server via ESM. And no I have no idea there is FIXUP SMTP option on the PIX. I will try to look up for the option and disable them to see whether there is any difference.
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Author Comment

by:nitrous_orangez
ID: 13713396
Sorry for the misinformation, we are currently using Sun Checkpoint Firewall ver 4.0 between mail01 and mail01 and not PIX firewall. Is there any setting in the Checkpoint that is equivalent to the FIXUP SMTP in PIX that should be disabled? I ran through the firewall config script and so far, found no entry on FIXUP SMTP. Any suggestion?
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Expert Comment

by:Sembee
ID: 13716487
No idea with the Checkpoint. FIXUP SMTP is what Cisco call it on the PIX. There may be an equivalent, probably with the word SMTP in its name. SMTP filtering, something like that.

You could try asking in the firewalls TA, somewhere there is bound to know.

Simon.
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Author Comment

by:nitrous_orangez
ID: 13723355
Ok, nevermind that. Last night I did another test,  I set up another exchange server to be yet another member of the current exchange org. Then from ESM, I set the new exchange server (mail04) as master (First admin group> routing groups > members > mail04 > master). I also created a new SMTP connector for mail04  using Internet Mail Wizard, no smarthost configured, set to send and received internet mail and using default virtual smtp of mail04 itself as local bridgehead, all pretty standard config , following the wizards' recommendations. Next, I went to the DNS server and change all the MX records that is pointing to mail01 to be pointed to mail04 (I just change the IP to IP of mail04) . By now all, incoming mail is accepted by mail04. Then, i sent from e-mail from my yahoo account to accounts residing in each of my exchange server (mail01/mail02/mail03/mail04) and surprisingly it was able to get through. And all the mail that were previously failed to be delivered (refer my first posting) are now able to get through succesfully without being stucked in any queues. I don't really know how this is possible because as far as i'm concern, the settings i had in my mail04 is the same settings that i have applied in mail01.

Or maybe you have another opinion/expalanation for that? Please help.
 
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Accepted Solution

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Sembee earned 1000 total points
ID: 13727395
There are any number of reasons why it could be working.
As you are now on a clean machine it does indicate that the issue was with the original machine. My instinct would say IIS or DNS. Actually diagnosing which was the source of the problem will be difficult. It may have been one of those that you would never have fixed unless the machine was rebuilt or at least IIS and Exchange reinstalled.

Simon.
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