After pressing the Send button on an email, the message stays in the outbox and Outlook only sends the message after a few hours. The problem does not seem related to a loss of connectivity to the server, and is not related to add-ins (as suggested at the website www.slipstick.com/problems/outbox.htm) as there are no Outlook add-ins installed. Outlook has been operating correctly in the past, so could this problem be due to a faulty Outlook program?

While having a corrupt installation of Outlook is unlikely to be causing this problem you describe, there is always an outside chance this could be causing the problem. So, the first procedure you could try is a repair installation on Microsoft Office, or completely reinstall Office. Completing a repair installation is the less intrusive process, so this should be attempted first. Go to the ‘Start’ menu > ‘Control Panel’ and open the ‘Add or Remove Programs’ control panel. Look through the list of installed programs and select the entry for Microsoft Office. Two buttons should appear and you need to click the ‘Change’ button. If this button does not appear, it seems the version of Office you are running does not support a repair installation. In this case, proceed to the next procedure outlining how to reinstall Outlook. Assuming the Change button is available, the Office setup should appear and in the list of options select ‘Reinstall or Repair’ and click ‘Next’. In the next screen, select the option ‘Detect and Repair errors in my Office installation’ and click ‘Install’. The repair installation should run and once this has completed, check whether the problem persists.

Should the problem continue, you could next try completely reinstalling Office. This should not cause any of your email messages to be lost, since the user mail store files are stored separately from the Outlook program files. Go back into the Add or Remove Programs window and uninstall Office. Once this has completed, restart the computer and then reinstall Office. Finally, restart the computer once again and check whether the problem persists. If the problem does continue, the issue is not related to a faulty installation of Outlook.

Since you have already found the problem is not related to any add-ins installed in Outlook, the next possible cause is third-party security software running on the computer. Many times I have encountered either firewall software or antivirus software scanning email messages and, for some reason or another, causing a large delay in the time at which emails are transmitted. If you have any third-party security software running (e.g. Norton, McAfee), try temporarily disabling the software to check whether the problem persists. For example, if you have an antivirus scanner with outbound email scanning, try disabling the email scanning feature. Be aware if you disable firewall software make sure you enable the Windows XP Firewall before disabling your third-party firewall, to provide at least a basic level of protection for your computer while the other firewall is disabled. The Windows XP Firewall can be enabled by going to the ‘Start’ menu > ‘Control Panel’ and opening the ‘Windows Firewall’ control panel (you may need to first click the ‘Network and Internet Connections’ category). Should the problem be resolved after disabling the antivirus or firewall software, this appears to be the cause of the issue. In this case, your best option is to visit the website for the manufacturer of the software to see whether an updated version is available, which may be able to resolve the issue, Alternatively, you may need to contact the software manufacturer to check whether a resolution is available. If you are still unsuccessful in resolving the issue, you may need to consider switching to another security software package which does not conflict with Outlook.

However, should the problem continue after disabling third-party security and antivirus software, then the next possibility is that the Outlook mail store PST file has become corrupt. We can test this theory by setting-up a mail store file, and redirecting the email to be delivered to the folder and for Outlook to use the new PST file when sending emails. Go to the ‘Tools’ menu > ‘Email Accounts’ and select ‘View or change existing e-mail accounts’ and click ‘Next’. Under the heading ‘Deliver new email to the following location’ click ‘New Outlook Data File’. Select ‘Office Outlook Personal Folders File (.pst)’ and click OK. Name the file something like ‘NewOutlook.pst’ and leave it in the default location, which should be:
C:Documents and SettingsLocal SettingsApplication DataMicrosoftOutlook.
Click OK to create the new file. A properties window will appear, and you should name the file ‘Personal Folders New’ (this will allow us to distinguish this new file from the old file). Leave all the other options at their defaults and click OK. At this stage you should be back in the E-Mail Accounts window. Under the heading ‘Deliver new email to the following location’ select ‘Personal Folders New’ in the drop-down box then click ‘Finish’. A message will appear informing you that this is now the default delivery location for new email. Click OK to confirm, and then restart Outlook. Be aware that all new email will now be delivered to the ‘Personal Folders New’ mail store. This means for the duration of this procedure, should any new email arrive it will be placed in the ‘Personal Folders New’ folder instead of the old ‘Personal Folders’ folder. This isn’t a big issue, as will be explained later, but you should be aware that this can happen.

Now that you are using the new mail store file, you need to try and send a message to check whether the problem is resolved. So, open a new email message and send a test message to yourself. If the message sends immediately, it seems the old folders were corrupted. In this case, you can just continue to use the new Personal Folders New for all future email. Since you will be using Personal Folders New you may wish to transfer your existing email from the old Personal Folders to this new folder structure. This is a simple process, and you just need to drag and drop the email from the old folder structure into the new folder structure.

However, should this not resolve the issue then it seems that a corrupt folder is not the cause of the issue. So, we need to do some cleanup at this stage to get rid of Personal Folders New. If any new emails did arrive during this procedure and ended up in the Personal Folders New inbox, they will need to be transferred back into the old Personal Folders structure. To do this, simply drag and drop the emails between locations to move the messages. Once this has been done, nothing should remain in Personal Folders New which you need to keep. So, we first need to change back the default delivery location for new email. Go to the ‘Tools’ menu > ‘Email Accounts’ and select ‘View or change existing e-mail accounts’ and click ‘Next’. Under the heading ‘Deliver new email to the following location’ select the old ‘Personal Folders’ option and click ‘Finish’ and OK in the confirmation box that appears. Restart Outlook and Personal Folders should now appear as the default folder structure. We can now close Personal Folders New and this will disappear from Outlook. In the mail folder listing, right-click on ‘Personal Folders New’ and select ‘Close ‘Personal Folders New”. This will now disappear from Outlook. Be aware, the actual PST data file will remain behind but this doesn’t really matter since the file will be very small and should not cause any problems.

If you reached this point and the problem is still unresolved I don’t have any further suggestions at this stage to help with the problem. So, should any other readers have suggestions or have experienced a similar problem then please write in with your suggestions!