I have exchange 2003 Enterprise SP2 running on Windows server 200 R2 SP2 in a clustered environment. We have been getting one or two messages stuck in the Outbound SMTP queue. The messages are in a retry state and stay there until they expire after 48 hours. They then send and NDR to the sender saying the timeout expired. We are using clustered IronPort devices as a smart hot for sending external e-mail. During the time that these messages are in the queue other messages are flowing OK. Even messages to the same host or recipient. It is not always the same sender or recipient or even domain that we have problems with. Exchange just seems to pick a message not to deliver. I have tracked them with Message tracking and they always end with being queued for remote delivery. I have also looked at the SMTP logs and do not see an attempt to deliver to the smart host. I see other messages being sent to the smart host but not the ones that are in retry. If we resend the same message it will go through. This happens even if we do not clear out the one that is stuck first. I do not see this every day but way too often. I have searched the internet and this forum but have not seen anything quite like this. Most of the articles apply when no messages are flowing. I am hoping that someone here may have seen this before or has an idea of something else to check Thanks in advance for your consideration. JRussell97

Have you enabled SMTP logging and looked at the logs?Ed Crowley MVP "There are seldom good technological solutions to behavioral problems."

Yes I have looked at the SMTP logs. I do not see any attempt to deliver the messages. I do see inbound messages and other outbound messages. The logs that I am talking about are set in the GUI of systems manager. Are there other logs to set and check? jrussell97

I'm talking about the SMTP protocol logs. http://support.microsoft.com/kb/821910 http://www.computerperformance.co.uk/exchange2003/exchange2003_logs_SMTP.htm Ed Crowley MVP "There are seldom good technological solutions to behavioral problems."

Hi 1. Download Microsoft Exchange Best Practices Analyzer v2.8 and scan your system http://www.microsoft.com/en-us/download/details.aspx?id=22485 2.Disable any antispam or antivirus feature. 3.Can you find any clue from this email? (send to same domain, contain same word ?) TechNet Subscriber Support in forum If you have any feedback on our support, please contact tngfb@microsoft.com

Yes Ed that is the logging that I am refering to. I went back and checked all of the parameters mentioned in the article that you referenced. All of the logging options are set. There is just nothing in the log that refers to those messages. It is like they go into the queue and then do nothing. Terence I have not run the best practices analyzer but all is working well for the most part. It is only occasionally that we see these messages trapped. Thanks Jrussell97

What SMTP connectors are defined on your system? Do any of them match the domain to which the messages are destined?Ed Crowley MVP "There are seldom good technological solutions to behavioral problems."

We only have one outbound smtp conector. it is called all-outbound-mail and is pointed to our Ironport devices. The Ironport acts as a smart host and sends the mail on to the internet after it goes through our filters. The problem is that the message does not make it to the Ironport for routing. There is not one sender or domain that is a problem. I have one stuck in the queue now that I had the user re-send. the second message went straight through. I looked at the SMTP logs and do not see any trace of the message at the original delivery time. I can however see the message when it was resent and went through sucessfully. I can see no ryme or reason for the message being stuck. It just sits there in retry status untill the timeout. THe retry count goes up if you look at the properties of the message in the queue. About the only thing that i see in common is that the ones that I have seen so far have all been calendar invitations. The users say that other types get stuck too but I have not seen one. It is not all calendar events that get stuck especially as we can send the same invite a second time and it goes through correctly. I can cut and paste sections of the log if you think that will help but I literally do not see any trace of the message. Thanks, jrussell97

Is there an error code showing in the queue viewer on the queue or message? If you can't find the activity in the SMTP protocol logs, I can't tell you where else to look.Ed Crowley MVP "There are seldom good technological solutions to behavioral problems."

At the bottom of the ESM screen under Additional Queue Information it says "Unable to open the message for delivery."

Based on seeing that message I have found a hotfix kb938650 that looks like it could help. I will try it.

Based on seeing that message I have found a hotfix kb938650 that looks like it could help. I will try it.

Hi Thanks for your update. 1. Install hotfix from kb:938650. 2. After you install the hotfix, you must create the FixRecipientTrackStatusTime register entry to enable the hotfix. To do this, follow these steps: 1. Click Start, click Run, type Regedit , and then click OK. 2. Locate the following registry subkey: HKEY_LOCAL_MACHINE\SYSTEM\CurrentControlSet\Services\MSExchangeIS\ParametersSystem\InternetContent\MimeHandlers\{85D2DDB8-6225-11D2-BDF1-00C04FD655B5} 3. On the Edit menu, point to New, and then click DWORD Value. 4. In the details pane, type FixRecipientTrackStatusTime for the new value, and then press ENTER. 5. Right-click FixRecipientTrackStatusTime, and then click Modify. 6. In the Edit DWORD Value dialog box, click Decimal under Base. 7. In the Value data box, type 1 , and then click OK. 8. Exit Registry Editor. 3. After performing the registry entries sometimes you will need to restart the Microsoft Exchange System Attendant serviceTerence Yu TechNet Community Support

We are still evaluating the Hot Fix. There is some internal discussion as to whether or not this is our problem. We are attempting to contact some of the companies that we are sending to so that we can find out if they are indeed running Exchange 2007. I will update this thread when we make a decision. Thanks for all your help, jrussell97

We are still evaluating the Hot Fix. There is some internal discussion as to whether or not this is our problem. We are attempting to contact some of the companies that we are sending to so that we can find out if they are indeed running Exchange 2007. I will update this thread when we make a decision. Thanks for all your help, jrussell97

We finally applied the hotfix last night. I have not seen any new messages stuck in the queue. Thanks jrussell97