We have a user who sends a email a couple times a week. When he sends the email, since most of the information is the same , he sends it to a group of people and includes himself. The next time he sends it he just takes the email he previously sent out, replies all, changes some of the text and sends it out. The email gets stuck in the mail queue under the domains he is attempting to send it to. He has been doing this since last year and the problem has just started occurring. It doesn't happen every time he does it just once in a while. When testing the email I have tried forwarding it to my hotmail and yahoo accounts and it gets stuck, if I send it internally it works. I have tried changing the subject, the text, even forwarding it blank and it still gets stuck. The only thing that seems to work is if I copy and paste the information into a new email. Since he has sent it out so many times we have tested some of the other emails and some work and some don't. I can send it via telnet but I am copying and pasting the data so it is not a true test. I have also tried it in OWA, on computers not in the domain,. computers with no virus software yet I still have the problem. Any help would be greatly appreciated. Also is there a way to test an email to see if it is corrupted?

Really wiered. When you run the message tracking , where exactly that gets stuck? Hopefully not in the categorizer due to any AV?? Is this exchange 2003 or 2007??Also see if the send connector is pointing to any smart host, if yes, try to remove the smart host and then try to relay emails directly to internet.Raj

Besides Raj's questions: Does the mail contain attachment? What's the last error of the queue? Is there any related error in event log? Seems like the specific mail's format is abnormal... Thanks, Elvis

Thank you both for replying Raj- We do not have AV on the server This is a snippet of the message in the queue SMTP:Message SUbmitted to Categorizer SMTP:Message Catorgorize and QUeed for Routing SMTP:Message Routed and QUeued for Remote Delivery SMTp:started OUtbound Transfer of Message Message Transferred to******************************** I tried removing the smart host, stopping and starting the smtp virtual server and still had the problem Elvis- The mail does not contain attachments..it is just a short message with text only no graphics or anything. I have tried to change the format from plain, to text to HTML and it still gets stuck. Like I said even if I clear out all the text in the message and subject and just forward it the message gets stuck. no errors in the event log.

I know this thread is pretty old, however I apperantly just ran into this issue. Here is what we found. The user has been doing this for about a year. We are running Exchange 2003 Enterprise SP2 on Windows 2003 Enterprise The user composed a generic email to send similar information to some of our customers. The next time the user needed it, he simply click forward in Outlook 2007, edited the message to reflect the new customer information, and clicked send. Again, the next time the user needed it, he took the newest of the forwared emails, and repeated the process. I had the user re-type the message in a new emal and sent it. The message was delivered without issue. We found that the size of the message that was sticking in the queue was 4 times the size of the newly typed email with the same content. These messages are being sent in HTML format. We compared the source code of the 2 emails and found that the message being forwared had much more formating code than the newly typed email. We believe that the receiving servers read this as some kind of virus or spam and was dropping the connection on that one email. I would appricate it anyone with another possible explination of what the receiving servers may have been doing or if someone can validate my conclusion. Thank you, Robert Ferguson

Thank you for responding. Very interesting. The issue is no longer occurring no reason why it is not. I don't recall there being an increase in file size, but all the other symptoms of the email issue sounds exactly the same. The software and OS's are a little different, which I am not sure makes a difference. Interested to see if others have had this problem.