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04.29.2008 at 03:49AM PDT, ID: 23361554
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6.6

EX03SP2 Message delivery fails between exchange servers

Asked by wellspokenman in Exchange Email Server, Symantec Anti-Virus Software, Cisco PIX Firewall

Tags: , , , ,

Hello,

I have two sites, three exchange servers and two domains. We are in the process of migrating. There is only one Exchange organisation. The problem is that mail sent from internal Outlook/OWA clients to mailboxes on the newly added exchange server in the remote site (ex03) is not being received.
 
ex01.olddomain.local - 10.1.1.10
ex02.newdomain.local - 10.1.1.11
ex03.newdomain.local - 10.1.2.10

Ex03 can send mail to users with mailboxes in the other two servers, and send and receive Internet mail via a connector - receiving email is the only problem. Sites are connected via an IPSEC tunnel and all other traffic/replication works very well.

From System Manager I notice that ex03 can see ex01 and ex02 with green ticks next to their names, but the same is not true for ex03 from ex02 or ex01. From these servers ex03 is either in perpetual active state with no error and a mounting queue, or it is in a retry state with one of three errors:
"the semaphore timeout period has expired"
"the remote server did not respond to a connection attempt"
"the connection was dropped by the remote host"

All 3 servers use their internal FQDN as the hostname in their default SMTP server.

Internet Message Filtering is not enabled on any of the SMTP servers.

All 3 servers can ping each others FQDNs, and ex02 + ex01 can both successfully deliver email to ex03 via telnet.

There is a single SMTP connector with a smart host and all 3 servers as bridgeheads. (I have tried creating a second routing group, second SMTP connector and a pair of routing group connectors - no luck)

--------------------------------some time later--------------------------
Further research into the semaphore errors seems to indicate that external security products can cause this issue. We do use a pair of PIXs and SAV was installed on all servers. I've since uninstalled Symantec AV from servers ex02 and ex03 and rebooted. No change in the behaviour. A PIX change request to remove ESMTP inspection has been submitted. These are the logs from the SMTP service of ex02 attempting to communicate with ex03

#Fields: date time c-ip cs-username s-sitename s-computername s-ip s-port sc-status sc-win32-status sc-bytes cs-bytes time-taken cs-host cs(User-Agent)

2008-04-29 08:26:06 10.1.2.10 OutboundConnectionResponse SMTPSVC1 ST-EX03 - 25 0 0 120 0 1250 - -
2008-04-29 08:26:06 10.1.2.10 OutboundConnectionCommand SMTPSVC1 ST-EX03 - 25 0 0 4 0 1250 - -
2008-04-29 08:26:06 10.1.2.10 OutboundConnectionResponse SMTPSVC1 ST-EX03 - 25 0 0 46 0 1313 - -
2008-04-29 08:26:06 10.1.2.10 OutboundConnectionCommand SMTPSVC1 ST-EX03 - 25 0 0 4 0 1641 - -
2008-04-29 08:26:06 10.1.2.10 OutboundConnectionResponse SMTPSVC1 ST-EX03 - 25 0 0 50 0 1703 - -
2008-04-29 08:26:06 10.1.2.10 OutboundConnectionCommand SMTPSVC1 ST-EX03 - 25 0 0 4 0 1703 - -
2008-04-29 08:26:06 10.1.2.10 OutboundConnectionResponse SMTPSVC1 ST-EX03 - 25 0 0 35 0 1766 - -
2008-04-29 08:26:06 10.1.2.10 OutboundConnectionCommand SMTPSVC1 ST-EX03 - 25 0 0 4 0 1766 - -
2008-04-29 08:26:06 10.1.2.10 OutboundConnectionResponse SMTPSVC1 ST-EX03 - 25 0 0 44 0 1828 - -

----------------------------------even more time later---------------------

here's something interesting:

2008-04-29 08:15:27 10.1.1.110 stupidserver SMTPSVC1 ST-EX02 10.1.1.11 0 250 0 49 17 0 - -
2008-04-29 08:15:39 10.1.1.110 stupidserver SMTPSVC1 ST-EX02 10.1.1.11 0 250 0 51 37 0 - -
2008-04-29 08:15:53 10.1.1.110 stupidserver SMTPSVC1 ST-EX02 10.1.1.11 0 250 0 37 33 0 - -

these logs were from my telnet sessions to ex02 - and the message was successfully delivered to the recipient with a mailbox over at ex03. So it seems it is only messages generated by OWA or Outlook that are not delivered across the site link.

I know that Symantec Mail Security used to be installed on server ex01 (the old domain) over a year ago. I've uninstalled SAV from ex01 as well, a reboot is scheduled for this evening.

So...congrats for getting this far: What I really need from the community is focus - I am troubleshooting too many things at once, and chasing rumours from forums. I am on the verge of reinstalling IIS and exchange - but I don't just want to do this on a hunch.

Your advice and time is greatly appreciated - thankyou. Start Free Trial
[+][-]04.29.2008 at 05:37AM PDT, ID: 21461555

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[+][-]04.29.2008 at 06:56AM PDT, ID: 21462283

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About this solution

Zones: Exchange Email Server, Symantec Anti-Virus Software, Cisco PIX Firewall
Tags: Microsoft, Exchange 2003, SP2, 3 EX03SP2 servers, two domains, two sites - mid migration., Semaphore timeout period has expired
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Solution Provided By: wellspokenman
Participating Experts: 1
Solution Grade: A
 
 
 
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