Email, Messaging, & Video Calls Email How to Send a File Attachment with Windows Live Hotmail 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 January 07, 2020 lucapierro / Getty Images Email Yahoo! Mail Gmail Tweet Share Email Email does not have to be only text. You can attach anything and send it along with your Windows Live Hotmail message: Word files, Excel spreadsheet documents, photos, zip files, you can send every single file on your computer to anybody with an email address. And doing it is simple in Hotmail! Send a File Attachment with Windows Live Hotmail To attach a file to a message in Windows Live Hotmail: ›› Step by Step Screenshot WalkthroughStart composing a new email message in Windows Live Hotmail.Click Attachments under Insert: in the message's toolbar.Find and highlight a file on your computer.Click Open or Choose, depending on your browser.Wait for the file to be completely uploaded.Continue editing the message.Eventually, click Send to deliver the message together with its attachments. Note that there is a size limit on the attachments you can send. For larger files, you should use a file sending service.