Dale from OR asks:

I can receive email messages with no problem in Outlook, but all my outgoing email stays in my Outbox and won’t send. Can you help?

Despite possibly being the world’s most ubiquitous e-mail program, Microsoft’s Outlook e-mail client is not without its flaws. Now in its 14th iteration, Microsoft Outlook is the de-facto e-mail program for home, small business, and corporate environments alike. While a massive amount of users, coupled with what has obviously been a long development time, have surely helped Microsoft to find and fix a number a errors in their code, a few bugs continue to show up in virtually every revision to date. One such bug: outgoing mail which does not leave the Outbox.

A persistent problem which has plagued users of Microsoft’s Outlook e-mail client for many, many years, a stubborn e-mail message which refuses to leave the outbox, when attempting to send. Besides the obvious frustration attempting to send and re-send an important e-mail unsuccessfully can cause, an additionally common side effect of an e-mail stuck in Outlooks’ outbox is the even more frustrating clogged outbox: a condition which Outlook will sometimes develop whereby not just a single problematic message, but every e-mail which you try to send from Outlook becomes stuck in the outbox upon initiating the Send or Send/Receive commands.

So what do you do when faced with a “clogged” Outlook outbox? While there are many theories as to why messages become stuck in the outbox, when pressed, even Microsoft has no definitive answer as to what the exact problem is, or how to fix it for good. However, there are a few options which will typically fix a clogged outbox, perhaps not for good, but for a good amount of time:

Option 1. Delete!

The easiest option that will, in my experience, fix a clogged outbox 9.5 times out of 10 is to simply delete any messages lingering in the outbox. Outlook seems to create errors within the outbox at odd times. When this happens, any messages which are then placed in the outbox with the un-sent message, as Outlook does when attempting to send any message, also become “corrupted” and will no longer send. It’s at this point which you want to save all your outgoing e-mail, clear the outbox, and restart Outlook. To do this, follow these steps:

Step 1. Open your outbox, and then open the message(s) you wish to save.

Step 2. Create a new e-mail message and copy and paste the content and recipient of your “corrupt” e-mail into this new e-mail.

Step 3. Save your new e-mail in your Drafts folder.

Step 4. Once all messages have been saved, select all e-mail messages in your outbox and click the Delete button.

Step 5. Shut down then re-open Outlook.

Step 6. Open the e-mails in your Drafts folder, and click Send

After a moment, your e-mails should leave your drafts folder, and finally be sent to their respective recipients.

If your e-mails are still stuck in your outbox, another option is to:

Option 2. Reboot your computer.

It sounds too simple to work, but many times just a simple reboot of your computer will actually fix a clogged outbox in Outlook. Just follow steps 1-4 above, shut off Outlook, then restart your computer and continue with steps 5-6. Surprisingly, this will actually fix a clogged outbox in some rare instances where Option 1 above does not work.

Finally, if all else fails, there is:

Option 3. Uninstall Outlook.

Unfortunately, sometimes your best bet for fixing Outlook is to remove and re-install the program. Doing this will hopefully allow any errant and/or corrupt files to be replaced with their original, working versions from your initial installation. Although un-installing and re-installing Outlook should fix any corrupt program files, the un-installation procedure may leave behind a corrupt file or two, which could potentially still cause problems with Outlook in the future. If you still wish to try un-installing Outlook to fix your Outlook outbox, follow these steps:

Step 1. Back up all your important e-mails and e-mail settings. There are a variety of ways to do this in Outlook, from exporting individual e-mails and settings, to purchasing full featured backup programs for Outlook. Once your data is backed up, click Start >Control Panel>Uninstall a Program.

Step 2. Under Uninstall or Change a Program, find the Microsoft Office icon, select it, and click the Change button at the top of the window.

Step 3. In the Microsoft Office dialog box which appears, click Add or Remove Features. The Installation Options list will appear.

Step 4. Find Microsoft Office Outlook in the list, click it, and select Not Available from the pop up list.

Step 5. Click the Continue button, and wait as Microsoft Office removes Outlook from your system.

Step 6. Once un-installation is complete, reboot your computer.

Step 7. When your computer boots back up, return to the Uninstall or Change a Program settings in the Control Panel, find the Microsoft Office icon, click Change, followed by Add or Remove Features, Microsoft Office Outlook, and select Run From My Computer followed by the Continue button to re-install Microsoft Outlook.

Step 8. Once installation is complete, reboot once again, startup Outlook, and restore your backup files.

There you have it; three (almost) surefire ways to fix a clogged out box in Microsoft Outlook. Happy E-mailing!

– J. Conboy