I have seen this happen to one other user as well once in a while. Mainly all 
of the messages that become stuck in the connector queue are from the one user. 
I have been able to replicate it by creating a meeting, inviting my external 
e-mail account and then canceling the meeting. My cancellation notifications 
will be stuck in the queue for a couple of days with numerous retries and then 
NDR with a 4.4.7. The original invitation will be delivered without a problem. 

I initially thought that maybe one of the stores was corrupted as it seemed to 
only be affecting calendar meeting requests. That is why the integrity checks 
were performed. 

All of the systems are manged by WSUS and Symantec Endpoint Manager and 
everything is up to date. Scans are run during the week and come up clean. 

The funny thing is this user has been on three different systems in his office, 
I have created new profiles, disabled auto-population of the address field and 
removed those contacts from his contacts list. We have tried with Anti-virus 
software diabled and uninstalled and it doesn't seem to matter. 

SMTP logging was enabled on the server, but I actually don't see very any 
messages other than this: 

application: warning - 2009/04/01 09:12:48 - MSExchangeTransport (327) - n/a 
"The following call : EcGetMime to the store failed. Error code : -2147467259. 
MDB 
: 2241c70c-055c-45da-8a25-ec4b43c13fa7. FID : 1-32. MID : 1-61D103. File : . 
For 
more information, click http://www.microsoft.com/contentredirect.asp."; 

There seems to be one of these for every item in the event log. This appears on 
the second server which contains the user mailboxes. 

When we send mail from the exchange server to the hosted server, we log in 
using an account made specifically for the exchange server so we don't actually 
use the user's logon ID when we send the e-mail. 

I have run the Exchange Troubleshooting Assistant and Best Practices Analyzer 
and neither came up with anything other than outdated drivers on the one 
server. 

I will follow the telnet testing procedures you provided and post the results. 

----- Original Message ----- 
From: "Peter Dahl" <peter.d...@yum.com> 
To: "MS-Exchange Admin Issues" <exchangelist@lyris.sunbelt-software.com> 
Sent: Wednesday, April 1, 2009 8:22:01 AM GMT -06:00 US/Canada Central 
Subject: RE: Item could not be opened error - Items stuck in queue 




FYI: This is the article I meant to reference for Telnet although both have the 
steps this one is easier to follow. http://support.microsoft.com/kb/323350 







From: Dahl, Peter [mailto:peter.d...@yum.com] 
Sent: Wednesday, April 01, 2009 9:15 AM 
To: MS-Exchange Admin Issues 
Subject: RE: Item could not be opened error - Items stuck in queue 



If this is only affecting one user then I would try another approach. 



· Is this client’s PC up to date on Windows security patches? Anti-Virus 
definitions? I would recommend a full system scan to ensure that the computer 
is not infected. 

· Create a new Outlook profile for that client and see if the problem still 
exists. 

· Have the client try using Outlook from another computer to see if the problem 
follows the account or if it is specific to his/her PC. 

· Have the client connect using OWA to rule out Outlook client issues. 



Since other people in your organization are able to send to the external 
recipient that is failing for the one client I would follow these 
troubleshooting steps to determine the root cause. 



· Verify that the client is using the correct smtp address for the external 
recipient 

· Again Telnet ( http://support.microsoft.com/kb/153119 ) is a great test to 
determine if you can send from your mail server to the recipient mail server. 
You could try one message from a sender that is able to send successfully then 
try another test from the sender who cannot to see if the response from the 
recipient server is different. (For example their spam filter could be silently 
blocking mail from that sender address) 

· Check SMTP logs to determine what is causing the message to timeout – you may 
have to enable and/or increase the protocol logging on your SMTP Virtual Server 
in Exchange 



Considering this is only affecting one user it is less likely that there is a 
problem with the Exchange server but I still recommend running Exchange Best 
Practices Analyzer on the server. Good luck and I hope that one of these steps 
will help you identify the root cause. 



Peter Dahl. 





From: Chris Larson [mailto:chr...@xp.etowns.net] 
Sent: Tuesday, March 31, 2009 3:11 PM 
To: MS-Exchange Admin Issues 
Subject: Re: Item could not be opened error - Items stuck in queue 




The ones that are stuck in the queue are going to external users. There are no 
issues with other people sending to the same external user. It mainly affects 
one user and I don't think that there is an attempt to contact the other 
server. I thought that there may have been some database corruption, but 
eseutil /k & /g check didn't show anything. 

----- Original Message ----- 
From: "Peter Dahl" <peter.d...@yum.com> 
To: "MS-Exchange Admin Issues" <exchangelist@lyris.sunbelt-software.com> 
Sent: Tuesday, March 31, 2009 4:05:36 PM GMT -06:00 US/Canada Central 
Subject: RE: Item could not be opened error - Items stuck in queue 



The fact that Outlook for your clients is going to a Not Responding state for 
30 minutes to 2 hours is what prompted the advice on checking server 
performance logs. 



On the messages getting stuck in the queue on Exchange, are they going to 
internal or external recipients or both? Are they all for the same domain or 
different domains? Can you successfully telnet from the Exchange server to the 
recipient mail server? 









From: Chris Larson [mailto:chr...@xp.etowns.net] 
Sent: Tuesday, March 31, 2009 12:16 PM 
To: MS-Exchange Admin Issues 
Subject: Re: Item could not be opened error - Items stuck in queue 




Both systems are exchange 2003. I'm not sure that it is a bottleneck issue as 
the messages never go out and eventually NDR with a 4.4.7. 

----- Original Message ----- 
From: "Peter Dahl" <peter.d...@yum.com> 
To: "MS-Exchange Admin Issues" <exchangelist@lyris.sunbelt-software.com> 
Sent: Tuesday, March 31, 2009 12:55:27 PM GMT -06:00 US/Canada Central 
Subject: RE: Item could not be opened error - Items stuck in queue 

You have multiple symptoms that may or may not be related. I would start by 
running the Exchange Best Practices Analyzer to verify if the Exchange server 
configuration is as you expect. I would also gather performance log data to 
determine where the bottleneck is occurring. I am not sure what version of 
Exchange you are running but these links may be helpful. 



Exchange 2003 Performance Troubleshooting Document: 

http://technet.microsoft.com/en-us/library/aa997270(EXCHG.65).aspx 

Exchange Server 2003 Performance: Ten Things to Think About 

http://technet.microsoft.com/en-us/library/aa996023(EXCHG.65).aspx 



Exchange 2007 Performance Counters and Thresholds 

http://msexchangeteam.com/archive/2008/07/01/449113.aspx 

Performance Issues - Applies to: Exchange Server 2007 SP1, Exchange Server 2007 

http://technet.microsoft.com/en-us/library/bb397229.aspx 









From: Chris Larson [mailto:chr...@xp.etowns.net] 
Sent: Tuesday, March 31, 2009 10:47 AM 
To: MS-Exchange Admin Issues 
Subject: Re: Item could not be opened error - Items stuck in queue 




Also I ran eseutil /k and /g on all of the stores and everything seems to be 
okay. 

----- Original Message ----- 
From: "Chris Larson" <chr...@xp.etowns.net> 
To: "MS-Exchange Admin Issues" <exchangelist@lyris.sunbelt-software.com> 
Sent: Tuesday, March 31, 2009 9:42:05 AM GMT -06:00 US/Canada Central 
Subject: Item could not be opened error - Items stuck in queue 


Hi, 

We have two exchange systems and we have an issue where certain e-mail are 
stuck at a retry status in our connector queue. These items will show numerous 
retries, but I can't see anything other that the message that the "Item could 
not be opened" down in the bottom of the queue viewer. 

There is also an issue with the users systems being very slow. Especially in 
the morning. Outlook will be at a "Not Responding" status for 30 to 120 
minutes. 

I have spent a lot of time trying to troubleshoot this and frankly everyone is 
pretty ticked off at this point. 

System setup. 

Exchange server #1: 

Runs fetchmail scripts to pull in mail from POP3 accounts at ISP and delivers 
to local SMTP for distribution 
Hosts account that we use to archive a copy of all e-mails from all accounts. 
Public folders stored here 

Exchange server #2 

All user accounts hosted on this server - copies of all e-mail are sent to 
account on serer #1 
All clients running Outlook 2007 









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Thank you for your cooperation. 





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