Troubleshooting Stuck Email in the Outbox

GFI MailEssentials and Send Policy FrameworkAdministration of Outlook will involve having to troubleshoot why emails sometimes get stuck in the email outbox.

There are times when clients are connected to your Exchange Server and your users are receiving their emails just fine. But when they attempt to send emails the emails get stuck in the email outbox. You open the Sent Items folder but you do not see the expected emails which indicate that they were not sent. Sometimes there are attachments and sometimes not, so this problem might appear random. All this can happen even while Outlook is connected.

Although users will have an imap connection configured for their email client no email can get sent through the Exchange Server. Sometimes your users’ data is stored in a local pst file and not on the Exchange Server.

They might also receive a Progress window that reports a Microsoft Exchange Server error message such as 0x80040115. It indicates that Exchange Server is unavailable and also indicates that Outlook is itself offline.

If you try to remove the message then Outlook will indicate that the message has already been sent but the process has not yet completed.

One possible solution is to exit Outlook and then delete the email in the outbox. You can do this by going to the lower left corner of the screen and click on the Start button to bring up your selections so that you can choose Run. In the Run window type “Outlook /safe”. Make sure you have a space between the word “Outlook” and the forward slash (/). Hit enter or click OK. You can then delete the email in the outbox.

How the send mail process is supposed to work is email should be moved to the outbox after an end user has clicked on the send button. Later, Outlook makes a connection to the email server, such as Exchange, and then tries to send the email. If successful then the sent email will show up in your outbox.

You should note that if you open and close the email message from within the outbox that this operation will cause the status to change and will result in the message not being sent. The email title will also no longer be italicised. You will have to click Send on the message toolbar if you want the message returned to send status. Later, when Outlook makes its connection to the Exchange Server, the message will be sent.

It is also possible that an end user’s personal folders have become damaged. Or their Personal Address Book files have become corrupted. You will need to repair those folders and files. I have outlined in previous posts how to make these corrections. This is also one of the reasons why email archiving is a recommended practice for all email administrators. Email archiving can be used to recover from corrupted folders and file. It is much easier to work with than having to repair corrupted folders and pst files.

An initial diagnostic step to perform is to run the Inbox Repair Tool. This tool will repair any damaged files. You must first identify the .pst file(s) you wish to repair. Obtain the full pathname and then run the Inbox Repair Tool and input the pathname to the .pst file(s) you wish to correct. You can run this tool by clicking on the Start button, pull right on Programs or All Programs, pull right on Accessories, pull right on System Tools, and then click on the Inbox Repair Tool. Follow the wizard steps to repair the questionable file(s).

Other solutions you can try is renaming any .pst and .ost files. You’ll have to locate those files on your systems, rename them and then create new profiles.

You may also have to check the Personal Address Book of your end user. Verify that the email address of the person they sent the email to is correct. You might even have to delete it and then add it in again.

Another diagnostic procedure you can perform is to try using another email client to send email to the recipient. If successful then you can compare the email dependent settings that are common to both clients and look for discrepancies that can be used to make corrections in the client configuration that is not sending emails.

You can also use “exchng32.exe” to send email using your existing services. If you are able to send email this way then you should try removing and then reinstalling Outlook.

Written by Mike Rede

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