Troubleshooting with Microsoft Exchange Troubleshooting Assistant

Email destined for the Internet kept getting stuck in queues on a Microsoft Exchange 2003 server. I could select the queue and force the email to be transmitted 1, but I wanted it to go out automatically. I didn't want to have to manually intervene anytime a message was sent to an external address.

After I emptied the queues with stuck email, a user sent a message to a mailing list and the message appeared to be stuck in an SMTP queue on the Exchange server again. So I downloaded the Microsoft Exchange Troubleshooting Assistant v1.12 , which can assist you in troubleshooting mail flow problems on Exchange servers 3.

When you install it, the default program location is C:\Program Files\ExTRA and the default data location is C:\Documents and Settings\Administrator\Application Data\Microsoft\ExTRA\.

To use the program, take the following steps:

  1. Click on Start.
  2. Select All Programs.
  3. Select Microsoft Exchange.
  4. Select Troubleshooting Assistant.
  5. When the program starts, check for updates by clicking on "Check for updates now".

    Exchange Troubleshooting Assistant check
for updates

  6. When the software has been updated, click on "Go to welcome screen."
  7. Click on "Select a task", which will bring up the Troubleshooting Task Select screen.
  8. Exchange Troubleshooting 
Assistant task selection

  9. Select a task to run. In this case I picked Mail Flow Troubleshooter.
  10. You will be asked to "enter an indentifying label for the analysis" and to select the symptoms you are seeing. The choces for symptoms are as follows:

    In this case I chose "Messages are backing up in one or more queues on a server." For the label, I entered "Stuck SMTP Queue 2007-06-17".
  11. Click Next.
  12. You will next be prompted for the Exchange Server Name. Enter the name of the server, which in my case was the same as the Global Catalog Server Name, which was another field on the same screen that was already filled.
  13. Click on Next.
  14. The Troubleshooting Assistant will then retrieve information and present you with an analysis of the problem. In my case it reported the following (Figure 1):

    Warning (exclamanation mark in yellow
triangle)   SMTP instance fully-qualified domain name does not match DNS resolved server name
    Warning (exclamanation mark in yellow
triangle)   SMTP instance fully-qualified domain name does not match server name

    Clicking on each issue listed will provide further information and may provide a "Tell me more about this issue and how to resolve it" link.

In this case, while I was troubleshooting, the message went out. So even though I received warnings regarding that the "SMTP instance FQDN does not match DNS resolved server name" 4, the mismatch did not prevent the message from going out, though there was a delay.

References:

  1. Email Stuck in SMTP Queues on Exchange Server
    Date: June 17, 2007
    MoonPoint Support
  2. Microsoft Exchange Troubleshooting Assistant v1.1
    Date Publisher: April 4, 2007
    Microsoft Download Center
  3. Mail Flow Troubleshooter in Exchange Troubleshooting Assistant (ExTRA) - A closer look
  4. SMTP instance FQDN does not match DNS resolved server name
    Last Modified: October 4, 2006
    Microsoft TechNet