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Mails queuing in SMTP Connector & delayed delivery

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Mails queuing in SMTP Connector & delayed delivery - 19.Apr.2007 3:54:18 PM   
chitrababu

 

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Joined: 19.Apr.2007
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Hi All,

Iam running Exchange 2003 server in cluster. The internet mails sent are delayed for varying time frame (30min, 40min, 1hr, 2hr etc). I have checked the queue in the gateway server, all the delayed mails sit in one of the SMTP connector for a long period. I have tried force connection, no go. No obvious event logs found. I have unhooked antigen 9.0 still it didn't solve. Used Microsoft Best Practice Analyser and results say that all those mails were unreachable destination. But those were all legitimate emails sent to our clients. Could anyone help me in resolving this issue.

_____________________________

Thanks and Regards,
Chitra Babu
Post #: 1
RE: Mails queuing in SMTP Connector & delayed delivery - 19.Apr.2007 4:22:35 PM   
uemurad

 

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Joined: 7.Jan.2004
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When you say delayed, do they eventually reach their destination, or do they ultimately fail?

Download and run the Troubleshooting Assistant from Microsoft.
http://www.microsoft.com/technet/prodtechnol/exchange/downloads/2003/tools.mspx

I'm curious if :
1. DNS is resolving correctly for the domains you are sending to
2. port 25 is open from your server to the receiving system

You can do these manually using NSLookup and Telnet respectively.

_____________________________

Regards,

Dean T. Uemura
Microsoft MVP - Exchange (2007-2011)
exchangeguy.blogspot.com
uemurad@yahoo.com

(in reply to chitrababu)
Post #: 2
RE: Mails queuing in SMTP Connector & delayed delivery - 19.Apr.2007 11:33:45 PM   
chitrababu

 

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Joined: 19.Apr.2007
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All the emails are delivered to the external domains eventually. The mails are not to one domain, there are multiple domains and all are stuck in the queue for long.

I have used Troubleshooting assistant, however it says that there could be orphaned routing group which is causing the problem. How do I remove these orphaned routing groups? Do you think this could be the cause, because the server was able to send mails prior to this as well.

Telnet to port 25 is successfull.


_____________________________

Thanks and Regards,
Chitra Babu

(in reply to uemurad)
Post #: 3
RE: Mails queuing in SMTP Connector & delayed delivery - 19.Apr.2007 11:49:57 PM   
chitrababu

 

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Joined: 19.Apr.2007
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The error message that I see in Troubleshooting assistant in Mail flow issues is:

"Possible orphaned address space."

It also gives a GUID, and the area it says is Link State. Not sure if this would be helpfull.

_____________________________

Thanks and Regards,
Chitra Babu

(in reply to uemurad)
Post #: 4
RE: Mails queuing in SMTP Connector & delayed delivery - 20.Apr.2007 9:54:36 AM   
uemurad

 

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How reliable is your Internet connection?  Do you experience frequent drop offs?

quote:

I have checked the queue in the gateway server, all the delayed mails sit in one of the SMTP connector for a long period

What does this connect to?  The outside?  Another server?  A smarthost?

_____________________________

Regards,

Dean T. Uemura
Microsoft MVP - Exchange (2007-2011)
exchangeguy.blogspot.com
uemurad@yahoo.com

(in reply to chitrababu)
Post #: 5
RE: Mails queuing in SMTP Connector & delayed delivery - 20.Apr.2007 10:22:10 AM   
chitrababu

 

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Joined: 19.Apr.2007
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The connector connects to anti-spam device/box called Iron Mail, and Iron mail sends out mail to internet.

The internet connection is highly reliable. I haven't seen much of drop offs.

I have enabled diagnostic logging for SMTP protocol and set it to max, and in the event viewer I can only see 7512 or 7515 event id's. These are related to IMF. Found nothing other than these event id's.

_____________________________

Thanks and Regards,
Chitra Babu

(in reply to uemurad)
Post #: 6
RE: Mails queuing in SMTP Connector & delayed delivery - 22.Apr.2007 1:43:07 AM   
uemurad

 

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Please clarify.  Are the messages being held in a queue on the Exchange server destined for the IronMail device, or are they on the IronMail device waiting to go to the Internet?

_____________________________

Regards,

Dean T. Uemura
Microsoft MVP - Exchange (2007-2011)
exchangeguy.blogspot.com
uemurad@yahoo.com

(in reply to chitrababu)
Post #: 7
RE: Mails queuing in SMTP Connector & delayed delivery - 22.Apr.2007 3:46:52 PM   
chitrababu

 

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Mails are queuing at the exchannge server, waiting to go to Iron Mail.

_____________________________

Thanks and Regards,
Chitra Babu

(in reply to uemurad)
Post #: 8
RE: Mails queuing in SMTP Connector & delayed delivery - 22.Apr.2007 5:29:19 PM   
uemurad

 

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Tell me if this summary fits.

1. Your Exchange server forwards outbound messages to the IronMail device via a smarthost setting.
2. The outbound messages are delayed in a queue on the Exchange server waiting to be delivered to the IronMail device.
3. The delayed messages indicate that the destination is unreachable.

Are the Exchange server and IronMail devices in the same subnet?
Are there other devices (besides a network switch) that the messages must pass through between Exchange and IronMail?
What does IronMail support have to say about your symptoms?

From the Exchange side, it just wants to forward the message to the next hop via port 25, looking for SMTP acknowledgement return codes.  If it doesn't get appropriate return codes, it will either give up (addressee doesn't exist), or queue for retrying.

_____________________________

Regards,

Dean T. Uemura
Microsoft MVP - Exchange (2007-2011)
exchangeguy.blogspot.com
uemurad@yahoo.com

(in reply to chitrababu)
Post #: 9
RE: Mails queuing in SMTP Connector & delayed delivery - 22.Apr.2007 6:10:08 PM   
chitrababu

 

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Joined: 19.Apr.2007
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The summary is correct.

There are no devices between exchange server and Iron Mail, except for Bright Mail (AntiSpam).

Exchange server and Iron mail are in same subnet or not, I need to check.

_____________________________

Thanks and Regards,
Chitra Babu

(in reply to uemurad)
Post #: 10
RE: Mails queuing in SMTP Connector & delayed delivery - 22.Apr.2007 6:19:19 PM   
uemurad

 

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Please continue the investigation of the subnet.

When I asked about other devices, I'm thinking more along the lines of routers, firewalls, and other devices that can possibly affect the flow of network traffic.  Either Exchange isn't able to communicate with IronMail (i.e. routing configuration, TCP port communication issue), or it isn't getting a proper acknowledgement from IronMail during the SMTP transmission.

On the Exchange server, can you telnet via port 25 to the IronMail server and create an entire message?  See how far into the process you can get before getting a negative response (e.g. 500-level return code).

Also, does the IronMail device have to be specifically configured for relaying?  If so, is your Exchange server allowed to relay through it?

_____________________________

Regards,

Dean T. Uemura
Microsoft MVP - Exchange (2007-2011)
exchangeguy.blogspot.com
uemurad@yahoo.com

(in reply to chitrababu)
Post #: 11
RE: Mails queuing in SMTP Connector & delayed delivery - 22.Apr.2007 9:56:35 PM   
chitrababu

 

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Joined: 19.Apr.2007
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If Exchange server is not able to communicate with Iron mail, Iam wondering how few mails are delivered via the same exchange server.

Iam able to telnet via port 25 from the exchange server to Iron mail successfully. Iron mail are configured to relay and our exchange server is allowed to relay through it only.

_____________________________

Thanks and Regards,
Chitra Babu

(in reply to uemurad)
Post #: 12
RE: Mails queuing in SMTP Connector & delayed delivery - 23.Apr.2007 12:17:55 AM   
uemurad

 

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If you manually create a complete message on the Exchange server telnetted to the IronMail device via port 25, address it from a valid address inside your domain and to a valid address outside your domain (including the message body), does it sit in the queue to the IronMail device?  Do you get any 500-level responses from IronMail, or do they all come back 200-level (OK)?  Does it return a code saying the message was accepted?

_____________________________

Regards,

Dean T. Uemura
Microsoft MVP - Exchange (2007-2011)
exchangeguy.blogspot.com
uemurad@yahoo.com

(in reply to chitrababu)
Post #: 13
RE: Mails queuing in SMTP Connector & delayed delivery - 27.Apr.2007 11:06:58 AM   
chitrababu

 

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Joined: 19.Apr.2007
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After manually creating message from exchange server I get the following result:
=======================================================================================
220 server.domain.com Microsoft ESMTP MAIL Service, Version: 6.0.3790.395
9 ready at  Fri, 27 Apr 2007 09:57:26 -0500
ehlo
250-server.domain.com Hello [158.107.69.11]
250-TURN
250-SIZE 30965760
250-ETRN
250-PIPELINING
250-DSN
250-ENHANCEDSTATUSCODES
250-8bitmime
250-BINARYMIME
250-CHUNKING
250-VRFY
250-X-EXPS GSSAPI NTLM
250-AUTH GSSAPI NTLM
250-X-LINK2STATE
250-XEXCH50
250 OK
mail from :chitra.babu@domain.com
250 2.1.0 chitra.babu@domain.com....Sender OK
Rcpt to:Externaladdress@externaldomain.com
250 2.1.5 Externaladdress@externaldomain.com
data
354 Start mail input; end with <CRLF>.<CRLF>
This is a test mail.
Regards,
chitra Babu
.
250 2.6.0 <ServerjtrSByh133tY00000560@server.domain.com> Queued mail for
delivery
============================================================================================

The Iron mail and Exchange server are in different subnets.

_____________________________

Thanks and Regards,
Chitra Babu

(in reply to uemurad)
Post #: 14
RE: Mails queuing in SMTP Connector & delayed delivery - 27.Apr.2007 11:27:57 AM   
uemurad

 

Posts: 8232
Joined: 7.Jan.2004
From: California, USA
Status: offline
Your telnet output indicates the receiving server accepted it and queued it.  It would appear not to be an Exchange issue.  Focus your troubleshooting on the IronMail device.  I do not have firsthand experience with IronMail, but I'd look to see if you can view its queues and if it has some sort of tracking.  If none of that works, I'd suggest talking to IronMail support passing along the telnet information.

_____________________________

Regards,

Dean T. Uemura
Microsoft MVP - Exchange (2007-2011)
exchangeguy.blogspot.com
uemurad@yahoo.com

(in reply to chitrababu)
Post #: 15

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