Microsoft Outlook is an e-mail client program that allows you to send and receive e-mail messages on the Internet. Sometimes an e-mail may get stuck in the outbox folder because of a large attachment or other connection issues. When this happens, every time you open Outlook, the program will continuously attempt to send the email and time out, preventing other mail from sending. You will need to delete this mail and recreate it to resend it in Outlook.
Launch the "Outlook" program on your computer.
Click on the "File" menu, then click "Work Offline." This will disconnect Outlook from the Internet and prevent it from attempting to send the email that is stuck.
Restart your Outlook program. Because you can't open a message that is in the process of sending, you will need to restart the program to have access to it. Outlook will remain in offline mode when you restart.
Click the "Outbox" folder in the left pane to see your unsent e-mail.
Double-click the email in the "Outbox" to open it.
Click "File," then click "Save As" to save a copy of the email to your computer. This will preserve the text in the email for resending.
Close the email to return to Outlook.
Right-click the email from the Outlook list, then click "Delete." This will remove the stuck e-mail from the outbox.
Click the "File" menu, and click "Work Offline" to restore the Internet connection to Outlook. Any unsent e-mail in the outbox should now send.
Locate the email file you saved earlier, and double-click the file to open it.
Hold down the "Ctrl" key on your keyboard and press the "A" key to highlight all of the email text. Press the "C" key while still holding the "Ctrl" key to copy the text.
Click "New" to create a new message in Outlook.
Hold down the "Ctrl" key on your keyboard and press the "V" key to paste the text in the new e-mail.
Make any edits to the email that you need, then click "Send" when you are ready to resend the email.
If the original message became stuck in the outbox because of an attachment, you should find a way to make the attachment smaller before resending. Do not attempt to resend the same attachment, as it will only cause the new message to become stuck.