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Messages stuck in queue

I have under 200 mails (less than 1MB in size each) stuck in my outgoing queue with initial delivery dates between Thursday & Friday Last week. These mails originated from two users in the organization, other mails have since successfully sent out leaving this set behind.
I'm currently running Exchange server 2003 sp2 on a Windows server 2003 OS.
Exchange is part of a local domain mycomany.local
My email domain is mycompany.org
Exchange sends the mail out using mycompanynamemail.mysysadminsdomain.com
Using DNS to send mails, (Tested with a SMTP connector, didn’t work)
Info about each queue says “unable to open the message for delivery”
Tested the public IP of my exchange server using MXTOOLBOX(SMTP):

 Not an open relay.
  0 seconds - Good on Connection time
  0.530 seconds - Good on Transaction time
  OK – xxx.xxx.xxx.xxx. resolves to mycompanynamemail.mysysadminsdomain.com
  OK - Reverse DNS matches SMTP Banner

 Stopped services for Symantec Mail security & Symantec endpoint, didn’t solve
Ran exchange best practice which found 3 critical issues:
1      System has more than 1gig and I should make some registry changes to correct.
2      Offline address book has no replication set
3      My email domain certificate has expired since April of this year and may cause some connectivity issues
Followed recommendations and corrected 1 & 2 (Ran test again and they are not showing as issues anymore) However I did not fully understand item 3 and so that critical issue is still pending.
The event viewer is not showing any errors pertaining to the queue.
I tried putting the message id of some of the mails in the queue in message tracking to see where its stopping but nothing comes up (not sure if I’m doing something wrong there).
DNS seems to be ok; however any advice on test to ensure same is welcome.
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Jamaicadood
Asked:
Jamaicadood
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1 Solution
 
R. Andrew KoffronCommented:
have you checked if your on any black lists for spam?
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JamaicadoodAuthor Commented:
Yes I did a blacklist test with mxtoolbox, IP is clean
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R. Andrew KoffronCommented:
what's the event viewer crying about?
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oztrodamusCommented:
Are the 200 emails going to recipients in the same company?
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JamaicadoodAuthor Commented:
No related messages in the event viewer, They are all outgoing messages to approximately 160 different domains
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oztrodamusCommented:
If you randomly pick out a couple of the domains and do a telnet <domain> 25, can you connect to the SMTP gateway's ok?
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JamaicadoodAuthor Commented:
I will test that now, However I am seeing a transport error in event log now.

Event Type:      Error
Event Source:      MSExchangeTransport
Event Category:      SMTP Protocol
Event ID:      7010
Date:            9/19/2010
Time:            10:47:31 PM
User:            N/A
Computer:      XXXXSERV1
Description:
This is an SMTP protocol log for virtual server ID 1, connection #5. The client at "xxx.xxx.xxx.xxx" sent a "rcpt" command, and the SMTP server responded with "550 5.7.1 Unable to relay for test@example.com  ". The full command sent was "rcpt TO: <test@example.com>".  This will probably cause the connection to fail.

For more information, click http://www.microsoft.com/contentredirect.asp.
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oztrodamusCommented:
It looks like the two clients don't have permission to email through the smtp virtual server.
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R. Andrew KoffronCommented:
I've had a couple servers get all backed up when someone had a virus was was sending out all sorts of bad messages, do the messages in the queue look legitimate?
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JamaicadoodAuthor Commented:
I did a couple telnet test on the domains in the queue and found that some connected while others didn't,
However I tested from another location to the ones that failed and they also failed there, Should I be able to telnet yahoo.com and hotmail.com and get a response?

Ignore the event log I sent it is actually when mxtoolbox does a smtp test to see if i have a open relay, which I don't hence the error.

The messages are authentic, bulk message. Its actually two separate emails sending to two different distribution list of their members.



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oztrodamusCommented:
If you look at the messages still in queue, does the queue message say if they have been grey listed?
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JamaicadoodAuthor Commented:
No
Info about each queue says “unable to open the message  for delivery” and I tried putting the message id of some of the mails in the queue in message tracking to see where its stopping but nothing comes up (not sure if I’m doing something wrong there).
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JamaicadoodAuthor Commented:
I deleted one of the messages with NDR and got the following:

Your message did not reach some or all of the intended recipients.
      Subject:  XXXXXXXXX
The following recipient(s) cannot be reached:
      XXXXXX  on 20/09/2010 9:16 AM
            This message was rejected due to the current administrative policy by the destination server.  Please retry at a later time.  If that fails, contact your system administrator.
            <xx.xxx.com #4.3.2>
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R. Andrew KoffronCommented:
how big are the messages? bad attachments maybe?
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R. Andrew KoffronCommented:
also try disabling anti-virus for a temperary test if your sure the outbound message is NOT a virus.

otherwise I'd delete the queue and see if the problem return or is a fluke.

your sender may be individually blacklisted on the servers in question you did say it was a bulk mail people sick of getting his mail?
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JamaicadoodAuthor Commented:
Messages are all under 1 mb and I had tested disabling anti virus system, Domain is not blacklisted and these are members who actually look forward to the info (user isn't spamming). Not sure i want to delete the queue just yet.


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JamaicadoodAuthor Commented:
I did some more digging and found some similarities. The messages stuck in the queue are all calender updates and i found an article on Microsoft site which is possibly whats happening to us (http://support.microsoft.com/kb/938650/en-us) it suggest that there is a problem in doing calender or meeting updates from exchange03 to exchange07 users. How can I confirm that the domains that are stuck in the queue do infact use exchange 2007 and also  I tried the fix it for me in the microsoft article but it states that it does not support my exchange server or OS but the document clearly states it is for exchange 03 sp2 which I'm running. Should I do the "Let me fix it myself" ?
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FDiskWizardCommented:
I just had to fix the Exchange 2003 <> 2007 meeting request bug on our Exchange 2003. We send back and forth with people a lot who use Exchange 2007, and the updated meetings were getting stuck in our queue. Worked for me... I'm on Exchange 2003 SP2 + updates...

I would be concerned why it isn't allowing you to install.
Check those files it is replacing, and look at your version numbers... I would hope they are all 6.5.xx?
You may want to apply other post-SP2 patches first.
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FDiskWizardCommented:
Or maybe you could try reinstalling SP2... then patches before the Hotfix.
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JamaicadoodAuthor Commented:
Thanks FdiskWizard did you do "the fix it for me" or you had to follow the "Let me fix it myself" by editing the registry.

I'm fully up to date where patches and service packs are concerned.
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JamaicadoodAuthor Commented:
Hotfix now installed and "fix it for me" worked, However messages are still in the queue. Should the messages that were in the queue before the patch now go out or do i need to delete them and have the user resend?
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JamaicadoodAuthor Commented:
Never mind queue has started to decrease, seems problem is solved. I will do some more test and watch it through today before I close.
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FDiskWizardCommented:
You did restart the required services after applying? Worked great for me... multiple servers.

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JamaicadoodAuthor Commented:
Im awarding FdiskWizward 250 points as i had already found the problem and post the solution, However i was having trouble installing the fix. Fdiskwizards post gave me the confidence that this was really the fix and allowed me to see my error in how i was installing the fix. Once that was done all worked great again.
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Computer_Service_PartnersCommented:
http://support.microsoft.com/kb/938650/en-us
This worked like a charm on a customers SBS2003 system.
Install hotfix, run fix it for me, restart services.
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craigzeiglerCommented:
thank you! worked like a charm.
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