Two mailstores, outgoing mail problem with SMTP connector/Smarthost

tnorman
tnorman used Ask the Experts™
on
I have an Exchange 2000 server, with two mailbox stores (one for each site).  There are two sites, 'Main' and 'Remote'.  These are connected via a VPN, and the users each access the same Exchange server the same way (just that the remote office uses Cached Mode).

I am having some delivery problems with the users at the remote site.  I think I have tracked the problem down to it not using the SmartHost.  The best example I can give are the headers of two emails from here, one successful (from main office) and one 'caught as spam failure'.

This is the (first part) of the headers for the successful email.  Note how it goes through a 'Telus' server, which is the SmartHost:

Return-path: <mainofficeuser@companydomain.COM>
Received: from pd5mr2no-ssvc.prod.shaw.ca
 (pd5mr2no-ssvc.prod.shaw.ca [10.0.153.213])
 by l-daemon (Sun Java System Messaging Server 6.2-7.05 (built Sep  5 2006))
 with ESMTP id <0KWZ00E4Q4SJYTP0@l-daemon> for myemail@shaw.ca; Thu,
 28 Jan 2010 13:26:43 -0700 (MST)
Received: from unknown (HELO pd6mi2no-ssvc.prod.shaw.ca) ([10.0.153.22])
 by pd5mr2no-svcs.prod.shaw.ca with ESMTP; Thu, 28 Jan 2010 13:26:43 -0700
Received: from unknown (HELO defout.telus.net) ([199.185.220.240])
 by pd6mi2no-dmz.prod.shaw.ca with ESMTP; Thu, 28 Jan 2010 13:26:43 -0700
Received: from edtnaa01.telusplanet.net ([142.179.219.146])
 by priv-edtnes27.telusplanet.net
 (InterMail vM.7.08.04.00 201-2186-134-20080326)
 with ESMTP id <20100128202756.XYDM27671.priv-edtnes27.telusplanet.net@edtnaa01.telusplanet.net>;
 Thu, 28 Jan 2010 13:27:56 -0700
Received: from mail.companydomain.COM
 (mail.companydomain.com [142.179.219.146])     by edtnaa01.telusplanet.net

 (BorderWare Security Platform) with ESMTP id 364DB0D1238A246B; Thu,
 28 Jan 2010 13:26:42 -0700 (MST)
Date: Thu, 28 Jan 2010 13:27:14 -0700

This is the (first part) of the headers for the failure email.  Note how it does NOT go through the Smarthost:

Return-path: <useratremoteoffice@companydomain.COM>
Received: from pd2mr1so-ssvc.prod.shaw.ca
 (pd2mr1so-ssvc.prod.shaw.ca [10.0.141.110])
 by l-daemon (Sun Java System Messaging Server 6.2-7.05 (built Sep  5 2006))
 with ESMTP id <0KWY00AQVV5LENV0@l-daemon> for myemail@shaw.ca; Thu,
 28 Jan 2010 09:58:33 -0700 (MST)
Received: from unknown (HELO pd3mi2so-ssvc.prod.shaw.ca) ([10.0.141.22])
 by pd2mr1so-svcs.prod.shaw.ca with ESMTP; Thu, 28 Jan 2010 09:58:30 -0700
Received: from unknown (HELO mail.companydomain.COM) ([142.179.219.146])
 by pd3mi2so-dmz.prod.shaw.ca with ESMTP; Thu, 28 Jan 2010 09:58:30 -0700
Date: Thu, 28 Jan 2010 09:59:01 -0700


The main issue is that when people send email from the remote office, it ends up in the Junk Folder of Hotmail, Yahoo, etc. etc.  I think I could solve this if I could figure out why emails from the remote office, even though they all go through the same Exchange server, one goes through the Smarthost and one does not.

Thanks for your time and help on this,

TN
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AkhaterSolutions Architect

Commented:
how many smtp virutal servers do you have ?

Author

Commented:
Just the one.
AkhaterSolutions Architect

Commented:
well that's more then weird

do you have a smtp connector? if so how is it configured ?
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Author

Commented:
Yes, there is an SMTP connector.  It is configured pretty plainly, just to use our ISPs mail server as a smart host.
AkhaterSolutions Architect

Commented:
when a user in the "remote site" sends an email do you see it in the queues ?

pause the smtp connector queue and try sending an email from the remote site and check if you can find it in that queue

Author

Commented:
I have now removed the connector, and only the VSMTP is delivering mail (with no Smarthost).

Still, emails to certain places (Hotmail, Yahoo) get caught as spam when sent from the remote site.

Author

Commented:
Further update: there is actually a third site connected via VPN, but their mailboxes are under the 'Main' mailbox store.  They can send emails without issue.  It has to have something to do with that particular store.
AkhaterSolutions Architect

Commented:
why did you remove the connector ? I don't get it?

did you try to pause the the smtp connector and check if the emails are on hold in the queue?

can you share a screenshot for the queues?

Author

Commented:
Akhater...thanks for your help here.   The troubleshooting leaves me to see that the issue is with the second/other store, not with the connector.  With our without the connector in place, the 'second store' behaves the same way.

I am going to close this question off, and start a new one with the specifics included (and not weighing so much about the connector).

Thanks for your help and time,

Tony
Solutions Architect
Commented:
It is your decision to close the question if you want but can you just do that test for me out of curiosity?

Author

Commented:
Problem resolved itself, awarded points to Ak for the effort and time.  Further details here:


http://www.experts-exchange.com/Software/Server_Software/Email_Servers/Exchange/Q_25100269.html

Author

Commented:
Problem resolved itself, awarding points for time/suggestions/effort from other member.

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