Email, Messaging, & Video Calls Email Delete Emails Stuck in the Windows Live Mail Outbox What to do when a message is stuck by Heinz Tschabitscher Writer A former freelance contributor who has reviewed hundreds of email programs and services since 1997. our editorial process Heinz Tschabitscher Updated on November 25, 2019 John Scrivener / Getty Images Email Yahoo! Mail Gmail Tweet Share Email Windows Live Mail is no longer available. This article remains for archival purposes only. When, once in a while and often due to an obscure cause, an email fails to send in Windows Live Mail, it may get stuck in the Outbox folder. This folder holds messages while they are in the process of being sent—from the time you have just clicked Send until the outgoing mail server's acknowledgment that the message has been received for delivery. In the Outbox, a message can linger and perpetually fail to send—until you remove it. Fortunately, deleting an email stuck in the Windows Live Mail Outbox is easy. Delete Emails Stuck in the Windows Live Mail Outbox To remove a message from the Outbox folder in Windows Live Mail when it persistently fails to send: Select Work offline in the Tools group of the Home tab. Select the View tab and choose Compact view in the ribbon if it is highlighted. Select Mail at the bottom of the folder list. Select Outbox in the list to open the Outbox. Select the message you want to delete and keep the mouse button pressed. Holding down the Ctrl key as well, drag the message to the Drafts folder for an account or Storage folders. Release the mouse button over Drafts, then release the Ctrl key. Now highlight the message you want to delete in the Outbox folder. Press Delete. You can also press Ctrl-D or select Delete in the Delete group of the Home tab. In the Drafts folder to which you copied the message the failed to send, you can now try double-clicking that email to edit it, fix any problems and attempt delivery again.