Email, Messaging, & Video Calls Email Use This Shortcut to Permanently Delete Messages in Windows Mail 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 June 24, 2019 Joli Ballew Email Yahoo! Mail Gmail Tweet Share Email How can you permanently delete a message without sending it to the trash folder? In the discontinued email clients Windows Live Mail, Windows Mail or Outlook Express, there is a shortcut to do this. This shortcut also works with Outlook.com. You can give it a try if you are still using one of those programs. This shortcut does not work with Mail for Windows 10. It is a desirable option when you spot a message you think may have a malicious attachment and you want it to be gone from your computer in a single step. If you simply hit the Del key, you will find these programs send the email to the trash instead of immediately getting rid of it completely. This is a nice safety net, but sometimes what you want is deletion without a net. How to Bypass the Trash To delete an email message immediately without utilizing the Recycle Bin in Windows Live Mail, Windows Mail or Outlook Express: Hold down the Shift key while pressing Del.Click Yes. It's important to be careful with this shortcut, though, since your message won't be recoverable once deleted this way with most programs. However, with Outlook.com, you can still recover permanently deleted items.