Email, Messaging, & Video Calls Email Email a File as an Attachment in Windows Live 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 June 14, 2019 Turnbull/Getty Images Email Yahoo! Mail Gmail Tweet Share Email Using Windows Mail or Outlook Express, it is easy to send text messages to friends, colleagues, and strangers. You can even use fancy stationery or insert pictures in your messages. But that's not all. You can also add any file to your emails and send it as an attachment to anybody equipped with an email address. Just ask before you send a large file. Send a file as an attachment with Windows Live Mail, Windows Mail or Outlook Express To send a file attached to an email with Windows Live Mail, Windows Mail or Outlook Express: Create a new message.Click the Attach button.Find and highlight the desired file in the Open or Insert Attachment dialog.You can highlight and attach multiple files at once by holding down the Ctrl key while you click on them with the mouse.Click Open or Attach, whichever you see. Sending multiple files with ease and elegance If you want to send more than one file with an email, you can also pack them neatly into one ZIP archive. And if you have the folder containing the file you want to attach open in Windows Explorer, you can alternatively, but easily, attach it by drag-and-drop.